Synthesis of 1,4-benzoxazines via Y(OTf)3-catalyzed ring opening/annulation cascade reaction of benzoxazoles with propargylic alcohols
Qi, Hongbo; Zhao, Yupeng; Li, Wencong; Chen, Shufeng; Chemical Communications  (2022) –; doi:10.1039/D2CC03080B

data_7130419
_publ_section_title
;
 Synthesis of 1,4-benzoxazines via Y(OTf)3-catalyzed ring
 opening/annulation cascade reaction of benzoxazoles with propargylic
 alcohols
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03080B
_journal_year                    2022
_chemical_formula_sum            'C22 H17 N O2'
_chemical_formula_weight         327.37
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2022-04-09 deposited with the CCDC.	2022-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.155(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6932(5)
_cell_length_b                   10.1353(5)
_cell_length_c                   18.2929(8)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.95
_cell_volume                     1707.69(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            37636
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0544P)^2^+0.3873P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1235
_reflns_number_gt                3244
_reflns_number_total             4245
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc03080b2.cif
_cod_data_source_block           mo_170605a_0m-auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1707.69(14)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7130419