Iridium-catalyzed intramolecular enantioselective allylation of quinazolin-4(3H)-one derivatives.
Peng, Fei; Tian, Hua; Zhang, Pengxiang; Yang, Haijun; Fu, Hua; Organic & biomolecular chemistry 17 (2019) 6461–6464; doi:10.1039/c9ob01057b

data_7156916
_publ_section_title
;
 Iridium-catalyzed intramolecular enantioselective allylation of
 quinazolin-4(3H)-one derivatives.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6461
_journal_page_last               6464
_journal_paper_doi               10.1039/c9ob01057b
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H21 N3 O'
_chemical_formula_sum            'C21 H21 N3 O'
_chemical_formula_weight         331.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-02-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.683(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1516(2)
_cell_length_b                   5.26734(13)
_cell_length_c                   17.9860(4)
_cell_measurement_reflns_used    5070
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      71.1260
_cell_measurement_theta_min      4.8240
_cell_volume                     864.11(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_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   -107.00 -14.00   1.00    1.00    --  -40.81 -57.00   0.00   93
  2  \w    -64.00  30.00   1.00    1.00    --  -40.81  57.00 150.00   94
  3  \w    -78.00  -3.00   1.00    1.00    --  -40.81 125.00-150.00   75
  4  \w    105.00 170.00   1.00    4.00    --  100.91 125.00-180.00   65
  5  \w    145.00 174.00   1.00    4.00    --  100.91 125.00 120.00   29
  6  \w     55.00 114.00   1.00    4.00    --  100.91-125.00-120.00   59
  7  \w     29.00  68.00   1.00    4.00    --  100.91-125.00  60.00   39
  8  \w     77.00 162.00   1.00    4.00    --  100.91  45.00 -60.00   85
  9  \w     74.00 172.00   1.00    4.00    --  100.91  30.00-120.00   98
 10  \w     93.00 118.00   1.00    4.00    --  100.91-125.00  60.00   25
 11  \w     29.00  55.00   1.00    4.00    --  100.91-125.00 150.00   26
 12  \w     76.00 104.00   1.00    4.00    --  100.91-125.00 150.00   28
 13  \w     32.00 126.00   1.00    4.00    --  100.91 -45.00  60.00   94
 14  \w     85.00 133.00   1.00    4.00    --  100.91  45.00   0.00   48
 15  \w     32.00 128.00   1.00    4.00    --  100.91 -61.00-150.00   96
 16  \w    -70.00 -27.00   1.00    1.00    --  -40.81 -38.00  90.00   43
 17  \w    -71.00 -10.00   1.00    1.00    --  -40.81 125.00 -60.00   61
 18  \w      8.00 101.00   1.00    1.00    --   40.81  77.00  90.00   93
 19  \w     78.00 107.00   1.00    1.00    --   40.81  77.00-120.00   29
 20  \w     23.00  73.00   1.00    1.00    --   40.81  77.00-120.00   50
 21  \w      8.00 108.00   1.00    1.00    --   40.81  77.00-180.00  100
 22  \w     10.00  64.00   1.00    1.00    --   40.81  77.00 -30.00   54
 23  \w     68.00  94.00   1.00    4.00    --  100.29  77.00-120.00   26
 24  \w     68.00 174.00   1.00    4.00    --  100.29  77.00  60.00  106
 25  \w    104.00 136.00   1.00    4.00    --  100.29  61.00  30.00   32
 26  \w     77.00 102.00   1.00    4.00    --  100.29  61.00  60.00   25
 27  \w     71.00  97.00   1.00    4.00    --  100.29  61.00 -60.00   26
 28  \w     71.00  96.00   1.00    4.00    --  100.29  61.00-150.00   25
 29  \w     68.00 148.00   1.00    4.00    --  100.29  77.00  30.00   80
 30  \w     71.00  97.00   1.00    4.00    --  100.29  61.00   0.00   26
 31  \w     73.00 148.00   1.00    4.00    --  100.29  61.00 120.00   75
 32  \w     73.00  99.00   1.00    4.00    --  100.29  61.00 -30.00   26
 33  \w     72.00 136.00   1.00    4.00    --  100.29  61.00-180.00   64
 34  \w     68.00  94.00   1.00    4.00    --  100.29  77.00 120.00   26
 35  \w    135.00 169.00   1.00    4.00    --  100.29  77.00 120.00   34
 36  \w     68.00  94.00   1.00    4.00    --  100.29  77.00 -60.00   26
 37  \w     76.00 102.00   1.00    4.00    --  100.29  61.00 -90.00   26
 38  \w     69.00  95.00   1.00    4.00    --  100.29  77.00  90.00   26
 39  \w     69.00  95.00   1.00    4.00    --  100.29  77.00-150.00   26
 40  \w     69.00  95.00   1.00    4.00    --  100.29  77.00 -30.00   26
 41  \w    140.00 166.00   1.00    4.00    --  100.29  77.00 -30.00   26
 42  \w     68.00  94.00   1.00    4.00    --  100.29  77.00   0.00   26
 43  \w    115.00 152.00   1.00    4.00    --  100.29  77.00   0.00   37
 44  \w     68.00  94.00   1.00    4.00    --  100.29  77.00 150.00   26
 45  \w     76.00 102.00   1.00    4.00    --  100.29  61.00-120.00   26
 46  \w     73.00  99.00   1.00    4.00    --  100.29  61.00 150.00   26
 47  \w     75.00 101.00   1.00    4.00    --  100.29  61.00  30.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0619247000
_diffrn_orient_matrix_UB_12      -0.0361452000
_diffrn_orient_matrix_UB_13      -0.0764177000
_diffrn_orient_matrix_UB_21      -0.1570327000
_diffrn_orient_matrix_UB_22      -0.0019704000
_diffrn_orient_matrix_UB_23      -0.0380904000
_diffrn_orient_matrix_UB_31      0.0066730000
_diffrn_orient_matrix_UB_32      0.2901851000
_diffrn_orient_matrix_UB_33      -0.0097200000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12553
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.514
_diffrn_reflns_theta_min         4.848
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1112 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3145
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0470P)^2^+0.0952P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0936
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.892
_reflns_Friedel_fraction_max     0.862
_reflns_number_gt                2966
_reflns_number_total             3145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01057b2.cif
_cod_data_source_block           20190219pengfei-whitebottle
_cod_depositor_comments          'Adding full bibliography for 7156916.cif.'
_cod_database_code               7156916
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 Ternary CH refined with riding coordinates:
 C00C(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00E(H00F,H00G), C00F(H00H,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00D(H00E), C00G(H00J), C00H(H00K), C00J(H00L), C00K(H00M),
 C00L(H00N), C00M(H00O), C00N(H00P)
2.d Idealised Me refined as rotating group:
 C00O(H00Q,H00R,H00S)
;
_shelx_res_checksum              23647
_shelx_hkl_checksum              93018
_olex2_date_sample_data_collection 2019-02-19
_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 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.642