Copper-catalyzed three-component <i>N</i>-alkylation of quinazolinones and azoles.
Wang, Chunlian; Ji, Xiaochen; Deng, Guo-Jun; Huang, Huawen; Organic & biomolecular chemistry 20 (2022) 1200–1204; doi:10.1039/d1ob02333k

data_7158497
_publ_section_title
;
 Copper-catalyzed three-component <i>N</i>-alkylation of quinazolinones
 and azoles.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1200
_journal_page_last               1204
_journal_paper_doi               10.1039/d1ob02333k
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C19 H19 N3 O2'
_chemical_formula_sum            'C19 H19 N3 O2'
_chemical_formula_weight         321.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-28 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                95.328(3)
_cell_angle_beta                 91.723(4)
_cell_angle_gamma                90.573(3)
_cell_formula_units_Z            4
_cell_length_a                   8.5358(4)
_cell_length_b                   9.3335(3)
_cell_length_c                   20.6119(9)
_cell_measurement_reflns_used    3945
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.5440
_cell_measurement_theta_min      2.1760
_cell_volume                     1634.16(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.963
_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    -89.00 -13.00   1.00    2.00    --  -40.73 125.00   0.00   76
  2  \w   -115.00   0.00   1.00    2.00    --  -40.73 -19.00 -90.00  115
  3  \w     23.00  50.00   1.00    2.00    --   40.73-125.00-180.00   27
  4  \w     23.00  54.00   1.00    2.00    --   40.73-125.00-150.00   31
  5  \w     47.00  86.00   1.00    2.00    --   40.73-125.00 -90.00   39
  6  \w     63.00 135.00   1.00    4.00    --  107.58 -61.00   0.00   72
  7  \w     82.00 177.00   1.00    4.00    --  107.58  30.00  90.00   95
  8  \w    106.00 133.00   1.00    4.00    --  107.58 125.00   0.00   27
  9  \w    109.00 147.00   1.00    4.00    --  107.58  45.00 -30.00   38
 10  \w     57.00  84.00   1.00    4.00    --  107.58 -45.00-150.00   27
 11  \w     83.00 108.00   1.00    4.00    --  107.58 -94.00-180.00   25
 12  \w     73.00 116.00   1.00    4.00    --  107.58-125.00-180.00   43
 13  \w     35.00 131.00   1.00    4.00    --  107.58 -45.00 -90.00   96
 14  \w     63.00 109.00   1.00    4.00    --  107.58 -94.00   0.00   46
 15  \w     44.00 156.00   1.00    4.00    --  107.58 -15.00  60.00  112
 16  \w     36.00 125.00   1.00    4.00    --  107.58 -61.00 120.00   89
 17  \w     33.00  58.00   1.00    4.00    --  107.58 -94.00  90.00   25
 18  \w     26.00 107.00   1.00    4.00    --  107.58 -94.00 -90.00   81
 19  \w   -115.00 -31.00   1.00    2.00    --  -40.73 -38.00-150.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0683751000
_diffrn_orient_matrix_UB_12      0.0815004000
_diffrn_orient_matrix_UB_13      -0.0558044000
_diffrn_orient_matrix_UB_21      0.0153963000
_diffrn_orient_matrix_UB_22      -0.1360239000
_diffrn_orient_matrix_UB_23      -0.0476527000
_diffrn_orient_matrix_UB_31      -0.1664216000
_diffrn_orient_matrix_UB_32      -0.0483825000
_diffrn_orient_matrix_UB_33      0.0159818000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11022
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.965
_diffrn_reflns_theta_min         4.311
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         6398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.3408P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5014
_reflns_number_total             6398
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02333k2.cif
_cod_data_source_block           x2
_cod_depositor_comments          'Adding full bibliography for 7158497.cif.'
_cod_database_code               7158497
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.86
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C18(H18A,H18B), C27(H27A,H27B), C28(H28A,H28B),
 C37(H37A,H37B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C29(H29),
  C32(H32), C33(H33), C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              84730
_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 1.478
_oxdiff_exptl_absorpt_empirical_full_min 0.312