Unprecedented transformation from cyclized zwitterionic oxazolidine derivatives to corresponding non-zwitterionic aromatic amides via Vilsmeier reagent in a one-pot reaction: optical property and crystallography
SD, Anwarhussaini; Mohitkar, Anuradha; Jayanty, Subbalakshmi; New Journal of Chemistry 46 (2022) 8069–8078; doi:10.1039/D2NJ00591C

data_7061400
_publ_section_title
;
 Unprecedented transformation from cyclized zwitterionic oxazolidine
 derivatives to corresponding non-zwitterionic aromatic amides via
 Vilsmeier reagent in a one-pot reaction: optical property and
 crystallography
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8069
_journal_page_last               8078
_journal_paper_doi               10.1039/D2NJ00591C
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C14 H13 N3 O2'
_chemical_formula_sum            'C14 H13 N3 O2'
_chemical_formula_weight         255.27
_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
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_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-07 deposited with the CCDC.	2022-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.9346(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   15.2072(2)
_cell_length_c                   13.27838(19)
_cell_measurement_reflns_used    5124
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9560
_cell_measurement_theta_min      4.4650
_cell_volume                     1215.08(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -11.00  19.00   0.50    7.00    --    0.00  82.00 120.00   60
  2  \w     59.00  89.00   0.50    7.00    --    0.00  82.00 120.00   60
  3  \w     -6.00  19.00   0.50    7.00    --    0.00 -19.00 -90.00   50
  4  \w    -79.00 -36.00   0.50    7.00    --    0.00 -19.00 -90.00   86
  5  \w     80.00 133.00   0.50    7.00    --   95.80  45.00 -90.00  106
  6  \w    141.00 167.00   0.50    7.00    --   95.80  45.00 -90.00   52
  7  \w     86.00 125.00   0.50    7.00    --   95.80 -77.00 -60.00   78
  8  \w     45.00 112.00   0.50    7.00    --   95.80 -82.00 -90.00  134
  9  \w      7.00 123.00   0.50    7.00    --   95.80 -77.00 120.00  232
 10  \w      8.00  34.00   0.50    7.00    --   95.80 -82.00 -90.00   52
 11  \w     73.00 178.00   0.50    7.00    --   95.80  61.00 120.00  210
 12  \w     70.00 105.00   0.50    7.00    --   95.80 -82.00  90.00   70
 13  \w     86.00 179.00   0.50    7.00    --   95.80  30.00-150.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0080109000
_diffrn_orient_matrix_UB_12      -0.0991903000
_diffrn_orient_matrix_UB_13      0.0222909000
_diffrn_orient_matrix_UB_21      -0.2515172000
_diffrn_orient_matrix_UB_22      0.0067509000
_diffrn_orient_matrix_UB_23      -0.0038911000
_diffrn_orient_matrix_UB_31      -0.0470583000
_diffrn_orient_matrix_UB_32      -0.0192598000
_diffrn_orient_matrix_UB_33      -0.1164532000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0107
_diffrn_reflns_av_unetI/netI     0.0090
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6120
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.094
_diffrn_reflns_theta_min         4.476
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0421P)^2^+0.5922P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2349
_reflns_number_total             2399
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj00591c2.cif
_cod_data_source_block           exp_207-jsl-11a
_cod_depositor_comments
'Adding full bibliography for 7061400--7061402.cif.'
_cod_database_code               7061400
_shelx_shelxl_version_number     2016/4
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C11(H11A,H11B), C14(H14A,H14B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C1(H1), C5(H5), C4(H4)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              96245
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.740
_oxdiff_exptl_absorpt_empirical_full_min 0.550