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_7230389
_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_formula_moiety         'C19 H18 Br N O4'
_chemical_formula_sum            'C19 H18 Br N O4'
_chemical_formula_weight         404.26
_chemical_melting_point          465
_chemical_name_common            'Benzoxazole Derivatives'
_chemical_name_systematic
'ethyl (E)-3-(2-(5-bromo-2-hydroxyphenyl)-5-methylbenzo[d]oxazol-3(2H)-yl)acrylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-06
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2017-03-27 deposited with the CCDC.
2018-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.215(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8540(7)
_cell_length_b                   9.8269(6)
_cell_length_c                   14.2696(11)
_cell_measurement_reflns_used    1820
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.2140
_cell_measurement_theta_min      4.1303
_cell_volume                     1797.6(2)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
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
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9908
_diffrn_measured_fraction_theta_max 0.9100
_diffrn_measurement_details
;
  1 omega  -15.00   24.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000  150.0000 39

  2 omega  -83.00   40.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178    0.0000  -60.0000 123

  3 omega  -38.00   29.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   57.0000   30.0000 67

  4 omega   -5.00   23.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000 -180.0000 28

  5 omega   -3.00   23.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000 -150.0000 26

  6 omega  -25.00    8.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000   60.0000 33
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0044370000
_diffrn_orient_matrix_UB_12      0.0707271000
_diffrn_orient_matrix_UB_13      -0.0084676000
_diffrn_orient_matrix_UB_21      0.0060438000
_diffrn_orient_matrix_UB_22      -0.0135092000
_diffrn_orient_matrix_UB_23      -0.0481982000
_diffrn_orient_matrix_UB_31      -0.0548049000
_diffrn_orient_matrix_UB_32      0.0042344000
_diffrn_orient_matrix_UB_33      -0.0097138000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10756
_diffrn_reflns_theta_full        29.28
_diffrn_reflns_theta_max         29.28
_diffrn_reflns_theta_min         4.14
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67843
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             757
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0619P)^2^+0.1847P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1371
_reflns_number_gt                2520
_reflns_number_total             4183
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ra01478g2.cif
_cod_data_source_block           exp-134
_cod_depositor_comments
;

2025-04-01
Z value and formula fixed to values more according to usual
chemical conventions.
The formula_sum item did not agree with the file content. It has
been replaced by the value given in formula_moiety.
                 miguel
;
_cod_original_formula_weight         734.57
_cod_original_formula_moiety         '2(C19 H18 Br N O4)'
_cod_original_formula_units_Z            2
_cod_original_formula_sum        'C36 H28 Br0.50 N3 O12'
_cod_database_code               7230389
_chemical_oxdiff_formula         'C36 H28 N3 O12'
_chemical_oxdiff_usercomment     '298K, PALE YELLOW COLOR ROD, 0.6 0.20 0.08'
_reflns_odcompleteness_completeness 99.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32