Palladium-Catalyzed Rearrangement Reaction to Access 1-Phenanthrol Derivatives
Liu, Ce; Shi, Wei-Yu; Ding, Ya-Nan; Zheng, Nian; Liang, Yong-Min; Chemical Communications  (2022) –; doi:10.1039/D2CC00392A

data_7129681
_publ_section_title
;
 Palladium-Catalyzed Rearrangement Reaction to Access 1-Phenanthrol
 Derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00392A
_journal_year                    2022
_chemical_formula_moiety         'C16 H14 O'
_chemical_formula_sum            'C16 H14 O'
_chemical_formula_weight         222.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-03-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-06-22 deposited with the CCDC.	2022-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.149(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9314(10)
_cell_length_b                   5.2194(3)
_cell_length_c                   13.7603(8)
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8240
_cell_measurement_theta_min      6.6630
_cell_volume                     1173.76(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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     -2.00  25.00   1.00    1.00    --    0.00  57.00   0.00   27
  2  \w     29.00  63.00   1.00    1.00    --    0.00  57.00   0.00   34
  3  \w     31.00  69.00   1.00    1.00    --    0.00  57.00 -90.00   38
  4  \w     35.00  63.00   1.00    1.00    --   54.00  77.00-120.00   28
  5  \w     36.00 118.00   1.00    1.00    --   54.00  57.00-120.00   82
  6  \w     79.00 104.00   1.00    2.00    --  108.00  77.00 -90.00   25
  7  \w    119.00 177.00   1.00    2.00    --  108.00  77.00-120.00   58
  8  \w    124.00 150.00   1.00    2.00    --  108.00 101.00 -13.00   26
  9  \w    150.00 177.00   1.00    2.00    --  108.00 111.00   0.00   27
 10  \w    121.00 174.00   1.00    2.00    --  108.00  77.00 -90.00   53
 11  \w    120.00 175.00   1.00    2.00    --  108.00  77.00-180.00   55
 12  \w    117.00 176.00   1.00    2.00    --  108.00  77.00-150.00   59
 13  \w    117.00 178.00   1.00    2.00    --  108.00  77.00 -30.00   61
 14  \w    122.00 174.00   1.00    2.00    --  108.00 111.00  30.00   52
 15  \w    100.00 147.00   1.00    2.00    --  108.00 111.00   0.00   47
 16  \w     91.00 119.00   1.00    2.00    --  108.00  50.00 -60.00   28
 17  \w     86.00 172.00   1.00    2.00    --  108.00  63.00 -60.00   86
 18  \w     94.00 121.00   1.00    2.00    --  108.00  50.00-120.00   27
 19  \w     87.00 115.00   1.00    2.00    --  108.00  63.00-150.00   28
 20  \w     88.00 116.00   1.00    2.00    --  108.00  50.00-150.00   28
 21  \w     82.00 109.00   1.00    2.00    --  108.00  38.00 -90.00   27
 22  \w     88.00 114.00   1.00    2.00    --  108.00  63.00 -90.00   26
 23  \w     83.00 109.00   1.00    2.00    --  108.00  38.00-120.00   26
 24  \w     83.00 108.00   1.00    2.00    --  108.00  38.00-150.00   25
 25  \w     87.00 112.00   1.00    2.00    --  108.00  63.00-180.00   25
 26  \w     80.00 107.00   1.00    2.00    --  108.00  77.00-150.00   27
 27  \w     79.00 104.00   1.00    2.00    --  108.00  77.00-180.00   25
 28  \w     78.00 104.00   1.00    2.00    --  108.00  77.00-120.00   26
 29  \w     86.00 117.00   1.00    2.00    --  108.00  50.00 -90.00   31
 30  \w     82.00 108.00   1.00    2.00    --  108.00  38.00 -60.00   26
 31  \w     83.00 110.00   1.00    2.00    --  108.00  38.00 -30.00   27
 32  \w     36.00  72.00   1.00    1.00    --   54.00 -57.00-120.00   36
 33  \w     27.00 104.00   1.00    1.00    --   54.00-125.00-120.00   77
 34  \w     49.00 138.00   1.00    2.00    --  108.00 -77.00  60.00   89
 35  \w     86.00 172.00   1.00    2.00    --  108.00  77.00 150.00   86
 36  \w     26.00  73.00   1.00    1.00    --   54.00  77.00 -60.00   47
 37  \w     15.00 125.00   1.00    1.00    --   54.00  19.00-180.00  110
 38  \w     -9.00  72.00   1.00    1.00    --   54.00 -57.00   0.00   81
 39  \w    -14.00  28.00   1.00    1.00    --    0.00  57.00 -90.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0372058000
_diffrn_orient_matrix_UB_12      -0.0595967000
_diffrn_orient_matrix_UB_13      0.0883951000
_diffrn_orient_matrix_UB_21      0.0819465000
_diffrn_orient_matrix_UB_22      -0.1175576000
_diffrn_orient_matrix_UB_23      0.0591945000
_diffrn_orient_matrix_UB_31      0.0280163000
_diffrn_orient_matrix_UB_32      0.2640572000
_diffrn_orient_matrix_UB_33      0.0462774000
_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  0.0191
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8338
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         6.506
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74975
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0030(7)
_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   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0756P)^2^+0.0610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1703
_reflns_number_total             2086
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00392a2.cif
_cod_data_source_block           liuc_0323
_cod_database_code               7129681
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C14(H14)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              42055
_shelx_hkl_checksum              8900
_olex2_date_sample_data_collection 2020-03-23
_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 1.731
_oxdiff_exptl_absorpt_empirical_full_min 0.664