Divergent synthesis of multi-substituted phenanthrenes <i>via</i> an internal redox reaction/ring expansion sequence.
Koyama, Ryosei; Anada, Masahiro; Sueki, Shunsuke; Makino, Kosho; Kojima, Tatsuhiro; Kawasaki-Takasuka, Tomoko; Mori, Keiji; Chemical communications (Cambridge, England) 60 (2024) 3822–3825; doi:10.1039/d4cc00797b

data_7132841
_publ_section_title
;
 Divergent synthesis of multi-substituted phenanthrenes <i>via</i> an
 internal redox reaction/ring expansion sequence.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3822
_journal_page_last               3825
_journal_paper_doi               10.1039/d4cc00797b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C20 H26 O4'
_chemical_formula_sum            'C20 H26 O4'
_chemical_formula_weight         330.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-20
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-01-09 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.1990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.10830(10)
_cell_length_b                   14.7871(2)
_cell_length_c                   22.9034(2)
_cell_measurement_reflns_used    7044
_cell_measurement_temperature    100.00(16)
_cell_measurement_theta_max      68.0520
_cell_measurement_theta_min      3.5450
_cell_volume                     3422.68(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (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      100.00(16)
_diffrn_detector                 'Rigaku HyPix-Bantam area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_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    -42.00 -16.00   0.50    0.20    --  -80.25  42.00 120.00   52
  2  \w    -28.00  23.00   0.50    0.20    --  -42.87  32.00 -30.00  102
  3  \w    -68.00 -16.00   0.50    0.20    --  -80.25  59.00 -60.00  104
  4  \w    -47.00 -14.00   0.50    0.20    --  -80.25  42.00-180.00   66
  5  \w    -28.00  20.00   0.50    0.20    --  -42.87  21.00-150.00   96
  6  \w    -17.00   9.00   0.50    0.20    --  -42.87  11.00-120.00   52
  7  \w    -28.00  21.00   0.50    0.20    --  -42.87  21.00 -90.00   98
  8  \w    -24.00  30.00   0.50    0.20    --  -42.87  11.00 150.00  108
  9  \w    -57.00  19.00   0.50    0.20    --  -42.87 101.00 -48.00  152
 10  \w   -103.00 -64.00   0.50    0.20    --  -42.87-138.00 150.00   78
 11  \w   -149.00-116.00   0.50    0.20    --  -80.25-101.00-152.00   66
 12  \w    -75.00 -47.00   0.50    0.20    --  -80.25 101.00 -48.00   56
 13  \w     26.00  53.00   0.50    0.20    --   42.87-101.00-152.00   54
 14  \w     85.00 122.00   0.50    0.20    --   94.32 -87.00-120.00   74
 15  \w     59.00 106.00   0.50    0.20    --   94.32-101.00-152.00   94
 16  \w     26.00  74.00   0.50    0.20    --   94.32 -87.00-120.00   96
 17  \w     77.00 103.00   0.50    0.20    --   94.32 -96.00 120.00   52
 18  \w     25.00  69.00   0.50    0.20    --   94.32 -96.00 120.00   88
 19  \w     -1.00  24.00   0.50    0.20    --   42.87 -11.00 150.00   50
 20  \w     30.00  61.00   0.50    0.20    --   94.32 -59.00 150.00   62
 21  \w     28.00  53.00   0.50    0.20    --   94.32 -59.00 120.00   50
 22  \w     28.00  53.00   0.50    0.20    --   94.32 -59.00  60.00   50
 23  \w     29.00  61.00   0.50    0.20    --   94.32 -59.00 -60.00   64
 24  \w     29.00  55.00   0.50    0.20    --   94.32 -50.00 -60.00   52
 25  \w     37.00  63.00   0.50    0.20    --   94.32 -59.00 -90.00   52
 26  \w     48.00  80.00   0.50    0.20    --   94.32 -68.00-120.00   64
 27  \w     36.00  61.00   0.50    0.20    --   94.32 -59.00-180.00   50
 28  \w     28.00  53.00   0.50    0.20    --   94.32 -50.00-120.00   50
 29  \w     28.00  53.00   0.50    0.20    --   94.32 -50.00 -30.00   50
 30  \w     28.00  53.00   0.50    0.20    --   94.32 -50.00  30.00   50
 31  \w     28.00  53.00   0.50    0.20    --   94.32 -50.00  60.00   50
 32  \w     28.00  53.00   0.50    0.20    --   94.32 -50.00 120.00   50
 33  \w     28.00  55.00   0.50    0.20    --   94.32 -50.00  90.00   54
 34  \w     88.00 161.00   0.50    0.20    --   94.32  25.00 -30.00  146
 35  \w     82.00 161.00   0.50    0.20    --   94.32  50.00 -90.00  158
 36  \w    120.00 146.00   0.50    0.20    --   94.32 101.00 -48.00   52
 37  \w    101.00 143.00   0.50    0.20    --   94.32 117.00 150.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-i'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0133193000
_diffrn_orient_matrix_UB_12      -0.0187110000
_diffrn_orient_matrix_UB_13      -0.0660272000
_diffrn_orient_matrix_UB_21      0.0481871000
_diffrn_orient_matrix_UB_22      -0.0976954000
_diffrn_orient_matrix_UB_23      0.0101020000
_diffrn_orient_matrix_UB_31      -0.1440151000
_diffrn_orient_matrix_UB_32      -0.0309886000
_diffrn_orient_matrix_UB_33      0.0080009000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9586
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.214
_diffrn_reflns_theta_min         3.558
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-i
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.479
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0440P)^2^+2.1700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2913
_reflns_number_total             3123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00797b2.cif
_cod_data_source_block           koyama_reduction_auto
_cod_depositor_comments
'Adding full bibliography for 7132841--7132842.cif.'
_cod_database_code               7132841
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H26O4
_shelx_estimated_absorpt_t_max   0.914
_shelx_estimated_absorpt_t_min   0.816
_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:
 C00H(H00K)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00D(H00D,H00E), C00F(H00G,H00H), C00G(H00I,H00J), C00K(H00P,
 H00Q), C00M(H00S,H00T)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00F), C00I(H00L), C00L(H00R)
2.d Idealised Me refined as rotating group:
 C00J(H00M,H00N,H00O), C00N(H00U,H00V,H00W), C00O(H00X,H00Y,H)
;
_shelx_res_checksum              95852
_shelx_hkl_checksum              15619
_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 1.134
_oxdiff_exptl_absorpt_empirical_full_min 0.824