Expect the unexpected - Li<sup>+</sup> migration governing the substitution of 7<i>H</i>-benzo[<i>de</i>]anthracene with main-group fragments.
Deka, Rajesh; Bhowmick, Toma; Orthaber, Andreas; Chemical communications (Cambridge, England) 62 (2026) 1900–1904; doi:10.1039/d5cc05878c

data_7135518
_publ_section_title
;
 Expect the unexpected - Li<sup>+</sup> migration governing the
 substitution of 7<i>H</i>-benzo[<i>de</i>]anthracene with main-group
 fragments.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1900
_journal_page_last               1904
_journal_paper_doi               10.1039/d5cc05878c
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C35 H39 P'
_chemical_formula_sum            'C35 H39 P'
_chemical_formula_weight         490.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-06-17 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.0692(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.72878(19)
_cell_length_b                   6.21523(7)
_cell_length_c                   25.4446(2)
_cell_measurement_reflns_used    29063
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      78.3030
_cell_measurement_theta_min      2.8660
_cell_volume                     2782.39(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 44.108a 64-bit (release 25-04-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_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   -122.00 -33.00   0.50    0.16    --  -48.15 -13.00  65.00  178
  2  \w    -50.00  27.00   0.50    0.16    --  -48.15  13.00-123.00  154
  3  \w    -26.00  44.00   0.50    0.16    --   48.15 -13.00  65.00  140
  4  \w     33.00 122.00   0.50    0.16    --   48.15  13.00-123.00  178
  5  \w   -177.00 -91.00   0.50    0.65    -- -106.00 -13.00  65.00  172
  6  \w     98.00 178.00   0.50    0.65    --  113.25  13.00-123.00  160
  7  \w    -25.00  44.00   0.50    0.16    --   48.15 -38.00   0.00  138
  8  \w    -25.00  44.00   0.50    0.16    --   48.15 -38.00 -60.00  138
  9  \w    -96.00 -33.00   0.50    0.65    -- -106.00  77.00  60.00  126
 10  \w    -73.00 -33.00   0.50    0.65    -- -106.00  61.00 -30.00   80
 11  \w    -96.00 -33.00   0.50    0.65    -- -106.00  77.00 -60.00  126
 12  \w   -112.00 -33.00   0.50    0.65    -- -106.00 125.00 -60.00  158
 13  \w    -96.00 -33.00   0.50    0.65    -- -106.00  77.00  30.00  126
 14  \w   -177.00 -92.00   0.50    0.65    -- -106.00 -15.00   0.00  170
 15  \w    -96.00 -33.00   0.50    0.65    -- -106.00  77.00 -30.00  126
 16  \w    -96.00 -33.00   0.50    0.65    -- -106.00  77.00 -60.00  126
 17  \w    -73.00 -33.00   0.50    0.65    -- -106.00  61.00  30.00   80
 18  \w    -73.00 -33.00   0.50    0.65    -- -106.00  61.00 -60.00   80
 19  \w    -73.00 -33.00   0.50    0.65    -- -106.00  61.00-150.00   80
 20  \w    100.00 178.00   0.50    0.65    --  113.25  15.00 -60.00  156
 21  \w     42.00 111.00   0.50    0.65    --  113.25-125.00-180.00  138
 22  \w     42.00 106.00   0.50    0.65    --  113.25 -95.00-150.00  128
 23  \w     42.00  90.00   0.50    0.65    --  113.25 -77.00 -90.00   96
 24  \w     42.00  90.00   0.50    0.65    --  113.25 -77.00 -30.00   96
 25  \w    101.00 178.00   0.50    0.65    --  113.25  45.00 150.00  154
 26  \w    100.00 178.00   0.50    0.65    --  113.25  15.00 -30.00  156
 27  \w   -120.00 -25.00   0.50    0.16    --  -48.15 -77.00-150.00  190
 28  \w   -120.00 -25.00   0.50    0.16    --  -48.15 -77.00  30.00  190
 29  \w   -120.00 -25.00   0.50    0.16    --  -48.15 -77.00 -60.00  190
 30  \w   -120.00 -25.00   0.50    0.16    --  -48.15 -77.00  60.00  190
 31  \w    -71.00  25.00   0.50    0.16    --  -48.15  77.00 120.00  192
 32  \w   -119.00 -33.00   0.50    0.16    --  -48.15 -57.00 -60.00  172
 33  \w   -120.00 -25.00   0.50    0.16    --  -48.15 -77.00 120.00  190
 34  \w   -177.00 -83.00   0.50    0.65    -- -106.00 -77.00-150.00  188
 35  \w   -177.00 -89.00   0.50    0.65    -- -106.00 -61.00 -90.00  176
 36  \w   -177.00 -83.00   0.50    0.65    -- -106.00 -77.00  30.00  188
 37  \w   -177.00 -83.00   0.50    0.65    -- -106.00 -77.00  90.00  188
 38  \w   -177.00 -89.00   0.50    0.65    -- -106.00 -61.00 150.00  176
 39  \w   -177.00 -89.00   0.50    0.65    -- -106.00 -61.00 -60.00  176
 40  \w   -177.00 -83.00   0.50    0.65    -- -106.00 -77.00   0.00  188
 41  \w   -177.00 -89.00   0.50    0.65    -- -106.00 -61.00-120.00  176
 42  \w   -177.00 -83.00   0.50    0.65    -- -106.00 -77.00 120.00  188
 43  \w    -73.00 -33.00   0.50    0.65    -- -106.00  61.00 120.00   80
 44  \w   -177.00 -83.00   0.50    0.65    -- -106.00 -77.00  60.00  188
 45  \w     42.00 111.00   0.50    0.65    --  113.25-125.00 150.00  138
 46  \w     42.00 106.00   0.50    0.65    --  113.25 -95.00  60.00  128
 47  \w    101.00 178.00   0.50    0.65    --  113.25  30.00 120.00  154
 48  \w   -120.00 -25.00   0.50    0.16    --  -48.15 -77.00-120.00  190
 49  \w   -120.00 -25.00   0.50    0.16    --  -48.15 -77.00 150.00  190
 50  \w   -121.00 -36.00   0.50    0.16    --  -48.15 -38.00  30.00  170
 51  \w   -120.00 -74.00   0.50    0.16    --  -48.15 -77.00   0.00   92
 52  \w    -26.00  37.00   0.50    0.16    --   48.15 -19.00-150.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0755724000
_diffrn_orient_matrix_UB_12      0.0360216000
_diffrn_orient_matrix_UB_13      0.0357535000
_diffrn_orient_matrix_UB_21      0.0435651000
_diffrn_orient_matrix_UB_22      -0.0208442000
_diffrn_orient_matrix_UB_23      -0.0485431000
_diffrn_orient_matrix_UB_31      -0.0074418000
_diffrn_orient_matrix_UB_32      0.2443459000
_diffrn_orient_matrix_UB_33      -0.0094230000
_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  0.0717
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            70008
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.354
_diffrn_reflns_theta_min         2.879
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.014
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024)
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 red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00066(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0449P)^2^+1.0439P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1047
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5050
_reflns_number_total             5916
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05878c2.cif
_cod_data_source_block           ao_rd_benzantpc_isomer3_auto
_cod_database_code               7135518
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C35 H39 P1 '
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.839
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C3(H3), C7(H7), C6(H6), C1(H1), C8(H8), C10(H10), C2(H2),
 C22(H22), C9(H9), C20(H20)
1.b Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C26(H26A,H26B,H26C), C33(H33A,H33B,H33C), C35(H35A,H35B,
 H35C), C30(H30A,H30B,H30C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C31(H31A,
 H31B,H31C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              93145
_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 1.328
_oxdiff_exptl_absorpt_empirical_full_min 0.786