A site-selective and stereospecific cascade Suzuki-Miyaura annulation of alkyl 1,2-bisboronic esters and 2,2'-dihalo 1,1'-biaryls.
Willems, Suzanne; Toupalas, Georgios; Reisenbauer, Julia C.; Morandi, Bill; Chemical communications (Cambridge, England) 57 (2021) 3909–3912; doi:10.1039/d1cc00648g

data_7128038
_publ_section_title
;
 A site-selective and stereospecific cascade Suzuki-Miyaura annulation of
 alkyl 1,2-bisboronic esters and 2,2'-dihalo 1,1'-biaryls.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3909
_journal_page_last               3912
_journal_paper_doi               10.1039/d1cc00648g
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H18 N4 O4'
_chemical_formula_sum            'C22 H18 N4 O4'
_chemical_formula_weight         402.40
_chemical_name_systematic
(S)-1-(2-(9,10-dihydrophenanthren-9-yl)ethylidene)-2-(2,4-dinitrophenyl)hydrazine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-01-07 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.79890(10)
_cell_length_b                   15.9461(2)
_cell_length_c                   30.2933(3)
_cell_measurement_reflns_used    76165
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.8090
_cell_measurement_theta_min      2.8960
_cell_volume                     3767.34(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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    -85.00   3.00   0.50    0.10    --  -10.00 -24.00-178.91  176
  2  \w    -88.00 -25.00   0.50    0.10    --  -26.00 148.00 104.89  126
  3  \w     16.00  43.00   0.50    0.10    --   46.00  90.00-145.80   54
  4  \w    -86.00 -40.00   0.50    0.10    --  -48.87 -44.00 146.38   92
  5  \w   -122.00 -88.00   0.50    0.10    --  -48.87 -44.00 146.38   68
  6  \w    -91.00 -39.00   0.50    0.10    --  -48.87 -30.00  43.78  104
  7  \w   -123.00 -96.00   0.50    0.10    --  -48.87 -30.00  43.78   54
  8  \w    -88.00 -38.00   0.50    0.10    --  -48.87 -44.00  -8.96  100
  9  \w     25.00  52.00   0.50    0.10    --   48.87  77.00  30.00   54
 10  \w     37.00  74.00   0.50    0.10    --   48.87  38.00 120.00   74
 11  \w     25.00  55.00   0.50    0.10    --   48.87  77.00 -30.00   60
 12  \w     33.00  82.00   0.50    0.10    --   48.87  57.00 -90.00   98
 13  \w     25.00  51.00   0.50    0.10    --   48.87  77.00-180.00   52
 14  \w     31.00  95.00   0.50    0.10    --   48.87-121.00 138.00  128
 15  \w     63.00 119.00   0.50    0.10    --   48.87 178.00 120.00  112
 16  \w     33.00  90.00   0.50    0.10    --   48.87  57.00 -30.00  114
 17  \w     77.00 124.00   0.50    0.10    --   48.87  38.00 120.00   94
 18  \w     34.00  63.00   0.50    0.10    --   48.87  57.00-180.00   58
 19  \w     25.00  65.00   0.50    0.10    --   50.00  80.00  96.36   80
 20  \w     33.00  59.00   0.50    0.10    --   58.00  80.00 147.29   52
 21  \w     35.00  61.00   0.50    0.10    --   58.00  80.00-144.62   52
 22  \w     76.00 119.00   0.50    0.10    --   58.00  80.00-144.62   86
 23  \w     37.00  69.00   0.50    0.10    --   62.00  80.00 -80.70   64
 24  \w     45.00  71.00   0.50    0.10    --   70.00  80.00 162.49   52
 25  \w     45.00  85.00   0.50    0.10    --   70.00  80.00  67.89   80
 26  \w    -74.00 -49.00   0.50    0.24    --  -70.00 -70.00 135.80   50
 27  \w     46.00  72.00   0.50    0.10    --   70.00  79.00-153.92   52
 28  \w     47.00  78.00   0.50    0.10    --   70.00  76.00  46.06   62
 29  \w     46.00  95.00   0.50    0.10    --   70.00  78.00 -16.40   98
 30  \w    -82.00 -48.00   0.50    0.24    --  -70.00 -73.00  60.24   68
 31  \w    110.00 136.00   0.50    0.10    --   70.00  80.00 162.49   52
 32  \w    114.00 140.00   0.50    0.10    --   74.00  80.00-129.44   52
 33  \w     92.00 117.00   0.50    0.10    --   74.00  80.00 -73.35   50
 34  \w     49.00  86.00   0.50    0.10    --   74.00  80.00 -73.35   74
 35  \w     49.00  74.00   0.50    0.10    --   74.00  80.00-129.44   50
 36  \w     50.00  78.00   0.50    0.10    --   74.00  79.00   7.02   56
 37  \w     52.00  78.00   0.50    0.10    --   74.00  73.00 -92.48   52
 38  \w     52.00  93.00   0.50    0.10    --   74.00  73.00 179.32   82
 39  \w     52.00  78.00   0.50    0.10    --   74.00  74.00 143.37   52
 40  \w     50.00  85.00   0.50    0.10    --   74.00  79.00 -51.98   70
 41  \w     99.00 139.00   0.50    0.10    --   74.00  78.00  31.67   80
 42  \w     50.00  76.00   0.50    0.10    --   74.00  78.00  31.67   52
 43  \w     94.00 144.00   0.50    0.10    --   78.00  76.00  95.61  100
 44  \w     55.00  83.00   0.50    0.10    --   78.00  76.00  95.61   56
 45  \w     57.00  82.00   0.50    0.10    --   78.00  71.00 -84.73   50
 46  \w     66.00  94.00   0.50    0.24    --   82.00  66.00-134.80   56
 47  \w    107.00 133.00   0.50    0.24    --   86.00  75.00 -34.02   52
 48  \w     63.00  94.00   0.50    0.24    --   86.00  75.00 -34.02   62
 49  \w    114.00 140.00   0.50    0.24    --   86.00  74.00 103.56   52
 50  \w     64.00 100.00   0.50    0.24    --   86.00  74.00 103.56   72
 51  \w     44.00 108.00   0.50    0.24    --   90.00-106.00 163.64  128
 52  \w     68.00 114.00   0.50    0.24    --   90.00  76.00 -31.65   92
 53  \w     70.00 100.00   0.50    0.24    --   90.00  69.00 -95.25   60
 54  \w     79.00 126.00   0.50    0.24    --   98.00  74.00  99.37   94
 55  \w    130.00 164.00   0.50    0.24    --   98.00  74.00  99.37   68
 56  \w     86.00 114.00   0.50    0.24    --  110.00  77.00  30.00   56
 57  \w     45.00 134.00   0.50    0.24    --  110.00 -77.00-120.00  178
 58  \w     94.00 162.00   0.50    0.24    --  110.00  57.00-180.00  136
 59  \w    101.00 128.00   0.50    0.24    --  110.00 -77.00  90.00   54
 60  \w     62.00  88.00   0.50    0.24    --  110.00 -77.00  90.00   52
 61  \w    122.00 176.00   0.50    0.24    --  110.00  77.00   0.00  108
 62  \w     86.00 116.00   0.50    0.24    --  110.00  77.00   0.00   60
 63  \w    131.00 165.00   0.50    0.24    --  110.00  77.00 120.00   68
 64  \w    133.00 177.00   0.50    0.24    --  110.00  60.00-170.52   88
 65  \w     86.00 113.00   0.50    0.24    --  110.00  77.00 120.00   54
 66  \w     93.00 125.00   0.50    0.24    --  110.00  60.00-170.52   64
 67  \w     80.00 113.00   0.50    0.24    --  110.00-125.00  30.00   66
 68  \w     98.00 140.00   0.50    0.24    --  110.00  38.00-120.00   84
 69  \w     92.00 126.00   0.50    0.24    --  110.00  63.00  27.36   68
 70  \w    142.00 176.00   0.50    0.24    --  110.00  57.00  60.00   68
 71  \w    102.00 127.00   0.50    0.24    --  110.00  57.00  60.00   50
 72  \w     86.00 161.00   0.50    0.24    --  110.00  77.00 -60.00  150
 73  \w     38.00  68.00   0.50    0.24    --  110.00 -57.00 -90.00   60
 74  \w     54.00 106.00   0.50    0.24    --  110.00 -99.00  90.00  104
 75  \w     93.00 118.00   0.50    0.24    --  110.00  77.00-120.00   50
 76  \w     41.00 106.00   0.50    0.24    --  110.00 -99.00  60.00  130
 77  \w     86.00 144.00   0.50    0.24    --  110.00  77.00  60.00  116
 78  \w     80.00 106.00   0.50    0.24    --  110.00 -99.00-120.00   52
 79  \w     86.00 174.00   0.50    0.24    --  110.00  77.00 -30.00  176
 80  \w     86.00 176.00   0.50    0.24    --  110.00  77.00 -90.00  180
 81  \w     46.00  75.00   0.50    0.24    --  110.00 -99.00-120.00   58
 82  \w     46.00 106.00   0.50    0.24    --  110.00 -99.00-180.00  120
 83  \w     99.00 124.00   0.50    0.24    --  110.00  38.00  30.00   50
 84  \w    121.00 173.00   0.50    0.24    --  110.00  77.00-120.00  104
 85  \w     86.00 172.00   0.50    0.24    --  110.00  77.00 150.00  172
 86  \w     42.00 103.00   0.50    0.24    --  110.00 -99.00   0.00  122
 87  \w    100.00 154.00   0.50    0.24    --  110.00  38.00 150.00  108
 88  \w    131.00 176.00   0.50    0.24    --  110.00  77.00-150.00   90
 89  \w     86.00 112.00   0.50    0.24    --  110.00  77.00-150.00   52
 90  \w    127.00 176.00   0.50    0.24    --  110.00  77.00  30.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0092361000
_diffrn_orient_matrix_UB_12      -0.0091405000
_diffrn_orient_matrix_UB_13      0.0505479000
_diffrn_orient_matrix_UB_21      0.1808295000
_diffrn_orient_matrix_UB_22      -0.0388491000
_diffrn_orient_matrix_UB_23      0.0001760000
_diffrn_orient_matrix_UB_31      0.0789762000
_diffrn_orient_matrix_UB_32      0.0879863000
_diffrn_orient_matrix_UB_33      0.0055542000
_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  0.0672
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            107452
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.394
_diffrn_reflns_theta_min         2.917
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane, pentane'
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 3303 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         8157
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0378P)^2^+1.2968P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                7894
_reflns_number_total             8157
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00648g2.cif
_cod_data_source_block           bm011120_1_1
_cod_depositor_comments          'Adding full bibliography for 7128038.cif.'
_cod_database_code               7128038
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C22H18N4O4
_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, All N(H) groups
2. Restrained distances
 N3B-H3B = N3A-H3A
 0.93 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C9A(H9A), C9B(H9B)
3.b Secondary CH2 refined with riding coordinates:
 C8A(H8AA,H8AB), C10A(H10A,H10B), C8B(H8BA,H8BB), C10B(H10C,H10D)
3.c Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2A(H2A), C4A(H4A), C7A(H7A), C12A(H12A), C13A(H13A), C14A(H14A),
 C15A(H15A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A), C1B(H1B), C2B(H2B),
  C4B(H4B), C7B(H7B), C12B(H12B), C13B(H13B), C14B(H14B), C15B(H15B),
 C18B(H18B), C19B(H19B), C20B(H20B), C21B(H21B)
;
_shelx_res_checksum              36153
_shelx_hkl_checksum              83800
_olex2_submission_original_sample_id bm011120_1_1
_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 1.376
_oxdiff_exptl_absorpt_empirical_full_min 0.730