A distal vinyl shift (DVS) through quadruple domino reaction: synthesis of N-vinyl benzoheterocyclic scaffolds
Bakthadoss, Manickam; Mushaf, Mohammad; RSC Advances 8 (2018) 12152–; doi:10.1039/C8RA01478G

data_7230390
_publ_section_title
;
 A distal vinyl shift (DVS) through quadruple domino reaction: synthesis
 of N-vinyl benzoheterocyclic scaffolds
;
_journal_issue                   22
_journal_name_full               'RSC Advances'
_journal_page_first              12152
_journal_paper_doi               10.1039/C8RA01478G
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_compound_source        No
_chemical_formula_moiety         'C18 H17 N O4'
_chemical_formula_sum            'C19 H18 N O3'
_chemical_formula_weight         308.34
_chemical_melting_point          475.15
_chemical_name_common            1,3-benzoxazine
_chemical_name_systematic
'methyl (E)-3-(2-(2-hydroxyphenyl)-2H-benzo[d][1,3]oxazin-1(4H)-yl)acrylate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-05-27
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;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_audit_update_record
;
2017-05-22 deposited with the CCDC.
2018-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5340(5)
_cell_length_b                   13.2552(10)
_cell_length_c                   15.2014(12)
_cell_measurement_reflns_used    1139
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.0261
_cell_measurement_theta_min      4.0109
_cell_volume                     1518.08(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9858
_diffrn_measured_fraction_theta_max 0.9011
_diffrn_measurement_details
;
  1 omega  -80.00  -49.00   1.0000   68.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000 -120.0000 31

  2 omega  -22.00    4.00   1.0000   68.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000 -120.0000 26

  3 omega  -39.00   -4.00   1.0000   68.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000  -90.0000 35

  4 omega   14.00   51.00   1.0000   68.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000  -90.0000 37

  5 omega  -25.00   25.00   1.0000   68.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  -90.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0063577000
_diffrn_orient_matrix_UB_12      -0.0376779000
_diffrn_orient_matrix_UB_13      0.0329628000
_diffrn_orient_matrix_UB_21      0.0134169000
_diffrn_orient_matrix_UB_22      -0.0378579000
_diffrn_orient_matrix_UB_23      -0.0322618000
_diffrn_orient_matrix_UB_31      0.0929308000
_diffrn_orient_matrix_UB_32      0.0028669000
_diffrn_orient_matrix_UB_33      0.0069257000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5373
_diffrn_reflns_theta_full        29.10
_diffrn_reflns_theta_max         29.10
_diffrn_reflns_theta_min         4.31
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             652
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.9(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0367P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                2333
_reflns_number_total             3203
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ra01478g2.cif
_cod_data_source_block           mb-mm-39
_cod_original_cell_volume        1518.09(19)
_cod_database_code               7230390
_chemical_oxdiff_formula         'C20 H18 N2 O2'
_chemical_oxdiff_usercomment     '298K, COLORLESS NEEDLE, 0.5 0.04 0.03'
_reflns_odcompleteness_completeness 98.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32