Facile synthesis of benzoxazole derivatives by a multi-component reaction catalysed by copper complexes capable of generating phenoxyl radical complex
Chaudhary, Virendra Kumar; Singh, Sain; Kumar, Kapil; Choudhury, Angshuman R.; Ghosh, Kaushik; New Journal of Chemistry 47 (2023) 18995–19004; doi:10.1039/D3NJ03160H

data_7062714
_publ_section_title
;
 Facile synthesis of benzoxazole derivatives by a multi-component reaction
 catalysed by copper complexes capable of generating phenoxyl radical
 complex
;
_journal_issue                   41
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18995
_journal_page_last               19004
_journal_paper_doi               10.1039/D3NJ03160H
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C26 H29 Cl2 Cu N3 O'
_chemical_formula_sum            'C26 H29 Cl2 Cu N3 O'
_chemical_formula_weight         533.96
_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             2021-04-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-12-01 deposited with the CCDC.	2023-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.271(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9524(5)
_cell_length_b                   12.3044(4)
_cell_length_c                   15.0863(6)
_cell_measurement_reflns_used    5205
_cell_measurement_temperature    296.0(2)
_cell_measurement_theta_max      27.8870
_cell_measurement_theta_min      2.6470
_cell_volume                     2574.46(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.939
_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    -69.00 118.20   0.30    3.00    --   29.89  54.00-180.00  624
  2  \w    -69.00 118.20   0.30    3.00    --   29.89  54.00   0.00  624
  3  \w    -69.00  20.10   0.30    3.00    --   29.89  54.00  90.00  297
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0439803000
_diffrn_orient_matrix_UB_12      0.0170442000
_diffrn_orient_matrix_UB_13      0.0240031000
_diffrn_orient_matrix_UB_21      0.0162684000
_diffrn_orient_matrix_UB_22      0.0188586000
_diffrn_orient_matrix_UB_23      -0.0402100000
_diffrn_orient_matrix_UB_31      -0.0203836000
_diffrn_orient_matrix_UB_32      0.0517416000
_diffrn_orient_matrix_UB_33      0.0067189000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29831
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.809
_diffrn_reflns_theta_min         2.511
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       plate
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.26
_refine_diff_density_max         1.147
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         8962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0568
_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^)+(0.1002P)^2^+0.4472P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.1933
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5356
_reflns_number_total             8962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj03160h2.cif
_cod_data_source_block           vc-0191_rt
_cod_depositor_comments
'Adding full bibliography for 7062713--7062714.cif.'
_cod_database_code               7062714
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C12(H12), C16(H16), C4(H4), C9(H9), C11(H11), C2(H2), C10(H10),
 C3(H3), C7(H7), C8(H8)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C), C26(H26A,H26B,H26C), C25(H25A,H25B,H25C)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.251
_oxdiff_exptl_absorpt_empirical_full_min 0.852