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_7135519
_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         'C29 H21 O P'
_chemical_formula_sum            'C29 H21 O P'
_chemical_formula_weight         416.43
_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             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                 94.7400(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.8945(3)
_cell_length_b                   5.60435(9)
_cell_length_c                   19.3173(4)
_cell_measurement_reflns_used    8542
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.7110
_cell_measurement_theta_min      4.5970
_cell_volume                     2038.54(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 44.97a 64-bit (release 03-03-2025))'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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 0.970
_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   -104.00 -46.00   0.50    2.00    --  -42.46 140.00-176.00  116
  2  \w    -81.00 -56.00   0.50    2.00    --  -42.46 130.00   9.00   50
  3  \w     66.00  91.00   0.50    2.00    --   42.46 140.00-176.00   50
  4  \w     35.00  61.00   0.50    2.00    --   42.46-130.00 -61.00   52
  5  \w     39.00  64.00   0.50    2.00    --   42.46-140.00 124.00   50
  6  \w     69.00  94.00   0.50    2.00    --   42.46 130.00   9.00   50
  7  \w   -148.00-123.00   0.50    8.00    -- -106.00-130.00 -61.00   50
  8  \w   -142.00-117.00   0.50    8.00    -- -106.00-140.00 124.00   50
  9  \w   -104.00 -76.00   0.50    8.00    -- -106.00 140.00-176.00   56
 10  \w    -92.00 -67.00   0.50    8.00    -- -106.00 130.00   9.00   50
 11  \w     47.00  92.00   0.50    8.00    --  117.50-130.00 -61.00   90
 12  \w     94.00 119.00   0.50    8.00    --  117.50 140.00-176.00   50
 13  \w    114.00 140.00   0.50    8.00    --  117.50 130.00   9.00   52
 14  \w    -50.00  35.00   0.50    2.00    --  -42.46  38.00 120.00  170
 15  \w    -41.00  37.00   0.50    2.00    --  -42.46  19.00-150.00  156
 16  \w    -34.00  43.00   0.50    2.00    --   42.46 -38.00 -30.00  154
 17  \w    -56.00 -31.00   0.50    8.00    -- -106.00  45.00-120.00   50
 18  \w    -70.00 -33.00   0.50    8.00    -- -106.00  61.00-120.00   74
 19  \w    -56.00 -31.00   0.50    8.00    -- -106.00  45.00   0.00   50
 20  \w    -69.00 -37.00   0.50    8.00    -- -106.00  61.00-150.00   64
 21  \w    -62.00 -34.00   0.50    8.00    -- -106.00 125.00 120.00   56
 22  \w    -56.00 -31.00   0.50    8.00    -- -106.00  45.00-180.00   50
 23  \w     45.00 178.00   0.50    8.00    --  117.50   0.00 120.00  266
 24  \w    151.00 176.00   0.50    8.00    --  117.50  30.00 -60.00   50
 25  \w     95.00 120.00   0.50    8.00    --  117.50  30.00 -60.00   50
 26  \w     80.00 110.00   0.50    8.00    --  117.50-125.00  60.00   60
 27  \w     56.00  85.00   0.50    8.00    --  117.50 -77.00 -90.00   58
 28  \w    102.00 134.00   0.50    8.00    --  117.50  30.00 -30.00   64
 29  \w    147.00 174.00   0.50    8.00    --  117.50  61.00   0.00   54
 30  \w     51.00  89.00   0.50    8.00    --  117.50 -77.00 -60.00   76
 31  \w    107.00 133.00   0.50    8.00    --  117.50  61.00   0.00   52
 32  \w     47.00  88.00   0.50    8.00    --  117.50 -77.00-180.00   82
 33  \w     49.00  80.00   0.50    8.00    --  117.50 -77.00  90.00   62
 34  \w     53.00  96.00   0.50    8.00    --  117.50 -95.00 -90.00   86
 35  \w    141.00 176.00   0.50    8.00    --  117.50  30.00 -30.00   70
;
_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      0.0418797000
_diffrn_orient_matrix_UB_12      -0.0086623000
_diffrn_orient_matrix_UB_13      0.0718468000
_diffrn_orient_matrix_UB_21      0.0690072000
_diffrn_orient_matrix_UB_22      -0.0469690000
_diffrn_orient_matrix_UB_23      -0.0350043000
_diffrn_orient_matrix_UB_31      0.0133501000
_diffrn_orient_matrix_UB_32      0.2707612000
_diffrn_orient_matrix_UB_33      -0.0037391000
_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  0.0205
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14072
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.304
_diffrn_reflns_theta_min         2.346
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.335
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.825
_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    1.357
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4287
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0616P)^2^+0.9117P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3945
_reflns_number_total             4287
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05878c2.cif
_cod_data_source_block           ao-rd-benzpo_auto
_cod_original_cell_volume        2038.55(6)
_cod_database_code               7135519
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C29  H21  O1  P1  '
_diffrn_oxdiff_digest_od_ed
;

;
_olex2_refinement_description
;
1. Restrained distances
 C24-C25A \\sim C24-C25B
 with sigma of 0.02
 C16-C1 \\sim C16-C1B
 with sigma of 0.02
 C1-C2 \\sim C1B-C2
 with sigma of 0.02
 C1-C2B \\sim C1B-C2B
 with sigma of 0.02
 C24-C29A \\sim C24-C29B
 with sigma of 0.02
 C27-C26A \\sim C27-C26B
 with sigma of 0.02
 C27-C28A \\sim C27-C28B
 with sigma of 0.02
 C26A-C25A \\sim C26B-C25B
 with sigma of 0.02
 C28A-C29A \\sim C28B-C29B
 with sigma of 0.02
 C24-C26A \\sim C24-C26B
 with sigma of 0.04
 C24-C28A \\sim C24-C28B
 with sigma of 0.04
 C27-C25A \\sim C27-C25B
 with sigma of 0.04
 C27-C29A \\sim C27-C29B
 with sigma of 0.04
2. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C1B)
3. Others
 Sof(H12)=Sof(C1B)=Sof(H1B)=Sof(C3B)=Sof(H3B)=Sof(C2B)=Sof(H2B)=1-FVAR(1)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(H11)=FVAR(1)
 Sof(H27A)=Sof(C26B)=Sof(H26B)=Sof(C29B)=Sof(H29B)=Sof(C25B)=Sof(H25B)=
 Sof(C28B)=Sof(H28B)=1-FVAR(2)
 Sof(H27)=Sof(C26A)=Sof(H26A)=Sof(C28A)=Sof(H28A)=Sof(C25A)=Sof(H25A)=
 Sof(C29A)=Sof(H29A)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C7(H7)
4.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C20(H20), C27(H27), C27(H27A), C23(H23), C19(H19), C8(H8), C5(H5),
 C22(H22), C6(H6), C9(H9), C26A(H26A), C28A(H28A), C25A(H25A), C4(H4), C10(H10),
  C29A(H29A), C1(H1), C2(H2), C3(H3), C12(H12), C26B(H26B), C29B(H29B),
 C25B(H25B), C28B(H28B), C1B(H1B), C11(H11), C3B(H3B), C2B(H2B)
;
_shelx_res_checksum              75739
_olex2_exptl_crystal_mounting_method 'Mitigen and Fomblin'
_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 1.629
_oxdiff_exptl_absorpt_empirical_full_min 0.797