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_7061402
_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         'C15 H16 Cl2 N4 O'
_chemical_formula_sum            'C15 H16 Cl2 N4 O'
_chemical_formula_weight         339.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-19 deposited with the CCDC.	2022-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.088(5)
_cell_angle_gamma                90
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_cell_length_b                   16.6928(8)
_cell_length_c                   7.6628(5)
_cell_measurement_reflns_used    5527
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.7420
_cell_measurement_theta_min      3.2730
_cell_volume                     1590.85(16)
_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)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.884
_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    -61.00 -18.00   0.50   45.03    --   -3.50 -37.00 120.00   86
  2  \w    -91.00   4.00   0.50   45.03    --   -3.50 -37.00-180.00  190
  3  \w    -29.00  -3.00   0.50   45.03    --    3.50 -37.00-120.00   52
  4  \w    -65.00 -36.00   0.50   45.03    --    3.50 -37.00-120.00   58
  5  \w      9.00  34.00   0.50   45.03    --    3.50 -82.00 -30.00   50
  6  \w    -85.00  -6.00   0.50   45.03    --    3.50 -82.00 -30.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0067177000
_diffrn_orient_matrix_UB_12      0.0046507000
_diffrn_orient_matrix_UB_13      0.0895911000
_diffrn_orient_matrix_UB_21      0.0457185000
_diffrn_orient_matrix_UB_22      -0.0244350000
_diffrn_orient_matrix_UB_23      0.0266634000
_diffrn_orient_matrix_UB_31      0.0334786000
_diffrn_orient_matrix_UB_32      0.0344354000
_diffrn_orient_matrix_UB_33      0.0068086000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17497
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.997
_diffrn_reflns_theta_min         3.167
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87522
_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    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         4485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0612P)^2^+2.1780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1547
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3509
_reflns_number_total             4485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj00591c2.cif
_cod_data_source_block           exp_342-j14r
_cod_depositor_comments
'Adding full bibliography for 7061400--7061402.cif.'
_cod_original_cell_volume        1590.85(15)
_cod_database_code               7061402
_shelx_shelxl_version_number     2016/4
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C5(H5), C2(H2), N4(H4), C4(H4A), C1(H1)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              41643
_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 1.155
_oxdiff_exptl_absorpt_empirical_full_min 0.881