One-pot, multicomponent, diastereoselective, green synthesis of 3,4-dihydro-2H-benzo[b][1,4]oxazine analogues.
Kushwaha, Narva Deshwar; Kushwaha, Babita; Karpoormath, Rajshekhar V.; Mahlalela, Mavela Cleopus; Shinde, Suraj Raosaheb; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00463

data_4038446
_publ_section_title
;
 One-pot, multicomponent, diastereoselective, green synthesis of
 3,4-dihydro-2H-benzo[b][1,4]oxazine analogues.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00463
_journal_year                    2020
_chemical_formula_moiety         'C21 H15 Cl N2 O4'
_chemical_formula_sum            'C21 H15 Cl N2 O4'
_chemical_formula_weight         394.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-26
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.5990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.59130(10)
_cell_length_b                   11.3803(2)
_cell_length_c                   17.0706(2)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    149.98
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.43
_cell_volume                     1831.50(4)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      149.98
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25266
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.612
_diffrn_reflns_theta_min         2.162
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0435 before and 0.0321 after correction.
The Ratio of minimum to maximum transmission is 0.9305.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4221
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0404P)^2^+0.8882P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3740
_reflns_number_total             4221
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00463_si_004.cif
_cod_data_source_block           19zs_rk_nd8_s49_etohac_0m
_cod_database_code               4038446
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.919
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 O3A-N2 \\sim O3B-N2
 with sigma of 0.02
 N2-O4A \\sim N2-O4B
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 N2, O3B, O4B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N2, O3A, O4A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(O3B)=Sof(O4B)=1-FVAR(1)
 Sof(O3A)=Sof(O4A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_shelx_res_checksum              23058
_shelx_hkl_checksum              96577
_olex2_submission_special_instructions 'No special instructions were received'