Ru(II)-Catalyzed and acidity-controlled tunable [5+1]/[5+2] annulation for building ring-fused quinazolines and 1,3-benzodiazepines.
Yang, Yurong; Zhang, Kaixin; Yang, Jian; Zhu, Guoxun; Chen, Weijie; Zhang, Chao; Zhou, Zhi; Yi, Wei; Chemical communications (Cambridge, England) 56 (2020) 11315–11318; doi:10.1039/d0cc04041j

data_7127060
_publ_section_title
;
 Ru(II)-Catalyzed and acidity-controlled tunable [5+1]/[5+2] annulation
 for building ring-fused quinazolines and 1,3-benzodiazepines.
;
_journal_issue                   76
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11315
_journal_page_last               11318
_journal_paper_doi               10.1039/d0cc04041j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C26 H23 N3'
_chemical_formula_sum            'C26 H23 N3'
_chemical_formula_weight         377.47
_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             2020-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-15 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                97.1840(10)
_cell_angle_beta                 94.2870(10)
_cell_angle_gamma                111.2000(10)
_cell_formula_units_Z            2
_cell_length_a                   9.03800(10)
_cell_length_b                   10.71960(10)
_cell_length_c                   10.86540(10)
_cell_measurement_reflns_used    18353
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9850
_cell_measurement_theta_min      4.1350
_cell_volume                     965.509(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_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   -117.00 -91.00   0.50    0.50    --  -46.37 -73.00 178.00   52
  2  \w    -49.00  14.00   0.50    0.50    --  -46.37  73.00 -52.00  126
  3  \w    -80.00 -24.00   0.50    0.50    --  -46.37 -73.00 178.00  112
  4  \w     25.00 110.00   0.50    0.50    --   46.37  73.00 -52.00  170
  5  \w     15.00  69.00   0.50    0.50    --   46.37 -73.00 178.00  108
  6  \w   -146.00 -80.00   0.50    1.00    -- -100.00 -73.00 178.00  132
  7  \w     83.00 150.00   0.50    1.00    --  105.44  73.00 -52.00  134
  8  \w     37.00 128.00   0.50    1.00    --  105.44 -73.00 178.00  182
  9  \w    -84.00 -59.00   0.50    0.50    --  -46.37 125.00 150.00   50
 10  \w   -108.00 -72.00   0.50    0.50    --  -46.37-125.00 -60.00   72
 11  \w     15.00  93.00   0.50    0.50    --   46.37-125.00-180.00  156
 12  \w   -108.00 -83.00   0.50    1.00    -- -100.00 -94.00 150.00   50
 13  \w    -59.00 -33.00   0.50    1.00    -- -100.00  77.00 150.00   52
 14  \w   -162.00-137.00   0.50    1.00    -- -100.00 -94.00 150.00   50
 15  \w    -99.00 -74.00   0.50    1.00    -- -100.00  73.00 -52.00   50
 16  \w   -174.00 -82.00   0.50    1.00    -- -100.00 -15.00-150.00  184
 17  \w    -68.00 -28.00   0.50    1.00    -- -100.00  45.00 150.00   80
 18  \w   -120.00 -63.00   0.50    1.00    -- -100.00  77.00 150.00  114
 19  \w   -114.00 -30.00   0.50    1.00    -- -100.00  45.00  30.00  168
 20  \w     37.00 108.00   0.50    1.00    --  105.44 -94.00-180.00  142
 21  \w    142.00 168.00   0.50    1.00    --  105.44  77.00-120.00   52
 22  \w     31.00 122.00   0.50    1.00    --  105.44 -15.00 -60.00  182
 23  \w     38.00  65.00   0.50    1.00    --  105.44 -94.00  60.00   54
 24  \w     85.00 136.00   0.50    1.00    --  105.44  77.00-120.00  102
 25  \w    134.00 178.00   0.50    1.00    --  105.44  15.00 -90.00   88
 26  \w     88.00 114.00   0.50    1.00    --  105.44  15.00 -90.00   52
 27  \w     57.00 104.00   0.50    1.00    --  105.44 -94.00 -30.00   94
 28  \w     71.00 100.00   0.50    1.00    --  105.44 -94.00  60.00   58
 29  \w     59.00 115.00   0.50    1.00    --  105.44-125.00  30.00  112
 30  \w     60.00  85.00   0.50    1.00    --  105.44 -94.00  30.00   50
 31  \w    -24.00  22.00   0.50    1.00    --   46.37 -72.00 178.00   92
 32  \w    -16.00  12.00   0.50    1.00    --   16.00  97.00-150.18   56
 33  \w      4.00  29.00   0.50    1.00    --   36.00  94.00  41.12   50
 34  \w     10.00  35.00   0.50    1.00    --   40.00  91.00 140.48   50
 35  \w    -48.00 -23.00   0.50    1.00    --  -46.37 -77.00 -30.00   50
 36  \w    -69.00 -32.00   0.50    1.00    --  -46.37 -38.00  30.00   74
 37  \w    -59.00 -24.00   0.50    1.00    --  -46.37 -77.00 -60.00   70
 38  \w     33.00  65.00   0.50    1.00    --   46.37  38.00  90.00   64
 39  \w     28.00  54.00   0.50    1.00    --   52.00  78.00  82.90   52
 40  \w    100.00 125.00   0.50    1.00    --   52.00  78.00  82.90   50
 41  \w     27.00  54.00   0.50    1.00    --   52.00  80.00 149.62   54
 42  \w     28.00  54.00   0.50    1.00    --   52.00  78.00-146.81   52
 43  \w     32.00  58.00   0.50    1.00    --   56.00  78.00-116.55   52
 44  \w     32.00  58.00   0.50    1.00    --   56.00  78.00-100.07   52
 45  \w     31.00  56.00   0.50    1.00    --   56.00  79.00 -69.75   50
 46  \w    -61.00 -35.00   0.50    1.00    --  -60.00 -79.00 -37.29   52
 47  \w   -131.00-105.00   0.50    1.00    --  -60.00 -79.00 127.02   52
 48  \w    -61.00 -35.00   0.50    1.00    --  -60.00 -79.00 127.02   52
 49  \w     35.00  61.00   0.50    1.00    --   60.00  80.00  15.90   52
 50  \w    -70.00 -44.00   0.50    1.00    --  -64.00 -82.00 162.07   52
 51  \w   -136.00-110.00   0.50    1.00    --  -64.00 -80.00  33.80   52
 52  \w    -66.00 -40.00   0.50    1.00    --  -64.00 -77.00  71.88   52
 53  \w    -65.00 -39.00   0.50    1.00    --  -64.00 -80.00  33.80   52
 54  \w     42.00  83.00   0.50    1.00    --   68.00  83.00-168.50   82
 55  \w     44.00  70.00   0.50    1.00    --   68.00  77.00-112.14   52
 56  \w    -71.00 -45.00   0.50    1.00    --  -72.00 -83.00 -41.64   52
 57  \w    -77.00 -51.00   0.50    1.00    --  -72.00 -71.00 100.50   52
 58  \w    -75.00 -50.00   0.50    1.00    --  -72.00 -72.00 -94.57   50
 59  \w    -81.00 -55.00   0.50    2.00    --  -76.00 -70.00 -11.11   52
 60  \w    -81.00 -55.00   0.50    2.00    --  -76.00 -74.00-158.43   52
 61  \w    -83.00 -58.00   0.50    2.00    --  -80.00 -73.00-165.91   50
 62  \w    -84.00 -58.00   0.50    2.00    --  -80.00 -75.00  79.44   52
 63  \w   -104.00 -55.00   0.50    2.00    --  -80.00 -83.00 173.70   98
 64  \w    -80.00 -54.00   0.50    2.00    --  -80.00 -81.00  43.39   52
 65  \w    -83.00 -57.00   0.50    2.00    --  -80.00 -78.00  72.72   52
 66  \w    -80.00 -54.00   0.50    2.00    --  -80.00 -83.00   0.05   52
 67  \w    -87.00 -61.00   0.50    2.00    --  -84.00 -80.00 152.60   52
 68  \w    -91.00 -66.00   0.50    2.00    --  -84.00 -61.00  84.23   50
 69  \w    -83.00 -58.00   0.50    2.00    --  -84.00 -82.00  43.39   50
 70  \w    -91.00 -65.00   0.50    2.00    --  -84.00 -67.00-140.03   52
 71  \w    -90.00 -64.00   0.50    2.00    --  -84.00 -67.00-118.51   52
 72  \w    -92.00 -67.00   0.50    2.00    --  -88.00 -69.00-179.40   50
 73  \w    -92.00 -66.00   0.50    2.00    --  -88.00 -72.00 -21.57   52
 74  \w    -91.00 -65.00   0.50    2.00    --  -88.00 -75.00 101.96   52
 75  \w    -95.00 -69.00   0.50    2.00    --  -88.00 -74.00 -53.97   52
 76  \w    -90.00 -64.00   0.50    2.00    --  -88.00 -77.00 -34.36   52
 77  \w    -92.00 -66.00   0.50    2.00    --  -88.00 -72.00  60.60   52
 78  \w    -92.00 -66.00   0.50    2.00    --  -88.00 -73.00 -88.20   52
 79  \w   -172.00-115.00   0.50    2.00    -- -100.00 -74.00 104.15  114
 80  \w   -147.00 -79.00   0.50    2.00    -- -100.00 -77.00  60.00  136
 81  \w   -118.00 -77.00   0.50    2.00    -- -100.00 -77.00   0.00   82
 82  \w   -108.00 -82.00   0.50    2.00    -- -100.00 -72.00 156.32   52
 83  \w   -125.00 -83.00   0.50    2.00    -- -100.00 -65.00  66.21   84
 84  \w   -168.00-124.00   0.50    2.00    -- -100.00 -77.00   0.00   88
 85  \w   -115.00 -78.00   0.50    2.00    -- -100.00 -77.00 150.00   74
 86  \w   -153.00-121.00   0.50    2.00    -- -100.00 -77.00 150.00   64
 87  \w   -105.00 -78.00   0.50    2.00    -- -100.00 -77.00  48.85   54
 88  \w   -166.00-141.00   0.50    2.00    -- -100.00 -77.00  48.85   50
 89  \w   -113.00 -81.00   0.50    2.00    -- -100.00 -72.00  91.34   64
 90  \w   -137.00-112.00   0.50    2.00    -- -100.00 -72.00 156.32   50
 91  \w   -159.00-133.00   0.50    2.00    -- -100.00 -78.00 -39.69   52
 92  \w   -102.00 -77.00   0.50    2.00    -- -100.00 -75.00 -26.22   50
 93  \w   -107.00 -81.00   0.50    2.00    -- -100.00 -64.00 -83.07   52
 94  \w   -145.00-119.00   0.50    2.00    -- -100.00 -75.00 -26.22   52
 95  \w   -173.00-136.00   0.50    2.00    -- -100.00 -72.00  91.34   74
 96  \w   -105.00 -79.00   0.50    2.00    -- -100.00 -74.00 136.42   52
 97  \w   -101.00 -76.00   0.50    2.00    -- -100.00 -76.00-146.22   50
 98  \w   -155.00-129.00   0.50    2.00    -- -100.00 -76.00-146.22   52
 99  \w   -102.00 -77.00   0.50    2.00    -- -100.00 -74.00  23.95   50
100  \w   -137.00-112.00   0.50    2.00    -- -100.00 -74.00  23.95   50
101  \w   -169.00-126.00   0.50    2.00    -- -100.00 -74.00 136.42   86
102  \w   -115.00 -77.00   0.50    2.00    -- -100.00 -78.00 -39.69   76
103  \w   -108.00 -82.00   0.50    2.00    -- -100.00 -61.00-150.00   52
104  \w    -66.00 -41.00   0.50    2.00    -- -100.00 125.00-150.00   50
105  \w   -115.00 -89.00   0.50    2.00    -- -100.00 125.00-150.00   52
106  \w   -127.00 -85.00   0.50    2.00    -- -100.00 -30.00  60.00   84
107  \w    -99.00 -74.00   0.50    2.00    -- -100.00 -81.00-172.62   50
108  \w   -172.00-125.00   0.50    2.00    -- -100.00 -81.00-172.62   94
109  \w   -108.00 -75.00   0.50    2.00    -- -100.00 -80.00  17.94   66
110  \w   -124.00 -76.00   0.50    2.00    -- -100.00 -77.00  30.00   96
111  \w   -110.00 -81.00   0.50    2.00    -- -100.00 -67.00 -84.73   58
112  \w   -102.00 -77.00   0.50    2.00    -- -100.00 -89.00 -91.13   50
113  \w   -161.00-135.00   0.50    2.00    -- -100.00 -77.00  30.00   52
114  \w   -107.00 -77.00   0.50    2.00    -- -100.00 -74.00 104.15   60
115  \w     80.00 106.00   0.50    2.00    --  107.00 125.00 150.00   52
116  \w     83.00 109.00   0.50    2.00    --  107.00  77.00-150.00   52
117  \w     98.00 123.00   0.50    2.00    --  107.00 -61.00-180.00   50
118  \w     85.00 123.00   0.50    2.00    --  107.00 -61.00   0.00   76
119  \w     53.00  78.00   0.50    2.00    --  107.00 -61.00-180.00   50
120  \w     36.00  62.00   0.50    2.00    --  107.00 -61.00   0.00   52
121  \w     57.00  98.00   0.50    2.00    --  107.00 -94.00 -60.00   82
122  \w     93.00 164.00   0.50    2.00    --  107.00  77.00   0.00  142
123  \w     90.00 116.00   0.50    2.00    --  107.00-125.00 150.00   52
124  \w     92.00 128.00   0.50    2.00    --  107.00  61.00-180.00   72
125  \w     54.00  80.00   0.50    2.00    --  107.00 -94.00-150.00   52
126  \w    146.00 177.00   0.50    2.00    --  107.00  61.00 -90.00   62
127  \w     84.00 109.00   0.50    2.00    --  107.00 -94.00 120.00   50
128  \w    140.00 176.00   0.50    2.00    --  107.00 125.00 150.00   72
129  \w    141.00 167.00   0.50    2.00    --  107.00  77.00-150.00   52
130  \w    -17.00  30.00   0.50    1.00    --   16.00  97.00-150.18   94
131  \w      4.00  36.00   0.50    1.00    --   36.00  94.00  41.12   64
132  \w     10.00  44.00   0.50    1.00    --   40.00  91.00 140.48   68
133  \w   -118.00 -30.00   0.50    1.00    --  -46.37 -57.00-180.00  176
134  \w   -140.00 -44.00   0.50    1.00    --  -68.00 -77.00 -70.82  192
135  \w   -140.00 -51.00   0.50    1.00    --  -68.00 -59.00  55.32  178
136  \w     42.00 134.00   0.50    1.00    --   68.00  83.00-168.50  184
137  \w   -145.00 -55.00   0.50    1.00    --  -72.00 -54.00 174.12  180
138  \w   -145.00 -56.00   0.50    1.00    --  -72.00 -55.00 -38.68  178
139  \w   -145.00 -53.00   0.50    1.00    --  -72.00 -66.00  80.29  184
140  \w   -145.00 -53.00   0.50    1.00    --  -72.00 -64.00 115.96  184
141  \w     51.00 149.00   0.50    1.00    --   76.00  80.00  82.45  196
142  \w    107.00 132.00   0.50    2.00    --  107.00  72.00 -51.00   50
143  \w    107.00 132.00   0.50    2.00    --  107.00  72.00 -51.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0422133000
_diffrn_orient_matrix_UB_12      0.1508122000
_diffrn_orient_matrix_UB_13      0.0522451000
_diffrn_orient_matrix_UB_21      -0.1062876000
_diffrn_orient_matrix_UB_22      -0.0408653000
_diffrn_orient_matrix_UB_23      0.1039987000
_diffrn_orient_matrix_UB_31      0.1446315000
_diffrn_orient_matrix_UB_32      0.0006425000
_diffrn_orient_matrix_UB_33      0.0850108000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1048
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            35376
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.934
_diffrn_reflns_theta_min         4.136
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0021(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0512P)^2^+0.3299P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3371
_reflns_number_total             3944
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04041j2.cif
_cod_data_source_block           fanwx_191028
_cod_depositor_comments
'Adding full bibliography for 7127060--7127061.cif.'
_cod_database_code               7127060
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.890
_diffrn_oxdiff_digest_frames
;
01e636b95384520beb903a31cee7f26f5603028d0f8
;
_diffrn_oxdiff_digest_hkl
;
01bc8b386e522fca60add06397af05c5fcbdb8
;
_reflns_odcompleteness_completeness 100.00
_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:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C26(H26), C21(H21), C9(H9), C25(H25), C11(H11), C23(H23), C24(H24),
 C20(H20), C19(H19), C17(H17), C10(H10), C18(H18)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              5962
_shelx_hkl_checksum              41659
_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 4.712
_oxdiff_exptl_absorpt_empirical_full_min 0.188