[Di(1-adamantyl)](aryl)phosphine ligands: synthesis, palladium complexation, and catalytic activity.
Sivarajan, Chinraj; Mitra, Raja; Dalton transactions (Cambridge, England : 2003) 54 (2025) 17073–17077; doi:10.1039/d5dt02523k

data_7719801
_publ_section_title
;
 [Di(1-adamantyl)](aryl)phosphine ligands: synthesis, palladium
 complexation, and catalytic activity.
;
_journal_issue                   46
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17073
_journal_page_last               17077
_journal_paper_doi               10.1039/d5dt02523k
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C21 H17 N'
_chemical_formula_sum            'C21 H17 N'
_chemical_formula_weight         283.36
_chemical_melting_point          429
_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     dual
_audit_creation_date             2025-10-14
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2025.07.01 svn.ra095ee60 for OlexSys, GUI svn.r7302)
;
_audit_update_record
;
2025-10-15 deposited with the CCDC.	2025-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.1550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.86120(10)
_cell_length_b                   17.1522(2)
_cell_length_c                   7.42200(10)
_cell_measurement_reflns_used    21435
_cell_measurement_temperature    105.2(8)
_cell_measurement_theta_max      74.9940
_cell_measurement_theta_min      3.7730
_cell_volume                     1476.12(3)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      105.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_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    -50.00  29.00   0.50    0.20    --  -43.02  54.00 -25.00  158
  2  \w   -114.00 -22.00   0.50    0.20    --  -43.02 -54.00-168.00  184
  3  \w    -29.00  45.00   0.50    0.20    --   43.02 -54.00-168.00  148
  4  \w     22.00  71.00   0.50    0.20    --   43.02  54.00 -25.00   98
  5  \w    -59.00 -30.00   0.50    0.82    -- -103.00  54.00 -25.00   58
  6  \w   -139.00-114.00   0.50    0.82    -- -103.00 -54.00-168.00   50
  7  \w     36.00  65.00   0.50    0.82    --  108.16 -54.00-168.00   58
  8  \w    132.00 157.00   0.50    0.82    --  108.16  54.00 -25.00   50
  9  \w   -113.00 -86.00   0.50    0.20    --  -43.02 -77.00  30.00   54
 10  \w    -56.00 -16.00   0.50    0.20    --  -43.02 -77.00  90.00   80
 11  \w    -57.00 -22.00   0.50    0.20    --  -43.02 -77.00 -90.00   70
 12  \w    -87.00 -16.00   0.50    0.20    --  -43.02 -77.00-180.00  142
 13  \w    -53.00 -20.00   0.50    0.20    --  -43.02 -57.00 -90.00   66
 14  \w    -62.00 -14.00   0.50    0.20    --  -43.02 -77.00  30.00   96
 15  \w     -1.00  38.00   0.50    0.20    --  -43.02  19.00 120.00   78
 16  \w   -115.00 -67.00   0.50    0.20    --  -43.02 -38.00 -60.00   96
 17  \w    -98.00 -64.00   0.50    0.20    --  -43.02 -77.00 -90.00   68
 18  \w    -57.00 -20.00   0.50    0.20    --  -43.02 -38.00 -60.00   74
 19  \w     15.00  59.00   0.50    0.20    --   43.02  77.00-180.00   88
 20  \w      8.00  42.00   0.50    0.20    --   43.02  90.00-100.04   68
 21  \w     22.00  73.00   0.50    0.20    --   43.02  57.00 120.00  102
 22  \w     14.00  70.00   0.50    0.20    --   43.02  77.00  30.00  112
 23  \w     46.00 122.00   0.50    0.20    --   43.02-178.00 120.00  152
 24  \w     53.00 122.00   0.50    0.20    --   43.02-178.00 -60.00  138
 25  \w   -107.00 -76.00   0.50    0.82    -- -103.00 -71.00 -81.24   62
 26  \w   -161.00-116.00   0.50    0.82    -- -103.00 -71.00 -81.24   90
 27  \w   -107.00 -79.00   0.50    0.82    -- -103.00 -61.00 -30.00   56
 28  \w   -164.00 -74.00   0.50    0.82    -- -103.00 -77.00 -30.00  180
 29  \w   -158.00-132.00   0.50    0.82    -- -103.00 -70.00-118.03   52
 30  \w   -113.00 -79.00   0.50    0.82    -- -103.00 -64.00 112.63   68
 31  \w   -154.00 -76.00   0.50    0.82    -- -103.00 -72.00-165.69  156
 32  \w   -101.00 -75.00   0.50    0.82    -- -103.00 -77.00  40.09   52
 33  \w   -116.00 -74.00   0.50    0.82    -- -103.00 -77.00-150.00   84
 34  \w   -108.00 -79.00   0.50    0.82    -- -103.00 -67.00   3.83   58
 35  \w   -116.00 -78.00   0.50    0.82    -- -103.00 -67.00-150.67   76
 36  \w   -173.00-134.00   0.50    0.82    -- -103.00 -64.00 -10.12   78
 37  \w   -105.00 -79.00   0.50    0.82    -- -103.00 -64.00 -10.12   52
 38  \w   -173.00-136.00   0.50    0.82    -- -103.00 -77.00-120.00   74
 39  \w   -107.00 -76.00   0.50    0.82    -- -103.00 -77.00  90.00   62
 40  \w   -153.00 -76.00   0.50    0.82    -- -103.00 -75.00 101.91  154
 41  \w   -174.00 -81.00   0.50    0.82    -- -103.00 -51.00 139.74  186
 42  \w   -163.00 -78.00   0.50    0.82    -- -103.00 -72.00  63.76  170
 43  \w   -110.00 -74.00   0.50    0.82    -- -103.00 -77.00 120.00   72
 44  \w   -174.00 -79.00   0.50    0.82    -- -103.00 -61.00-120.00  190
 45  \w   -145.00-120.00   0.50    0.82    -- -103.00 -77.00 120.00   50
 46  \w   -121.00 -74.00   0.50    0.82    -- -103.00 -77.00 150.00   94
 47  \w   -166.00-115.00   0.50    0.82    -- -103.00 -68.00 130.43  102
 48  \w   -146.00 -74.00   0.50    0.82    -- -103.00 -77.00-180.00  144
 49  \w   -162.00-136.00   0.50    0.82    -- -103.00 -69.00-142.30   52
 50  \w   -102.00 -77.00   0.50    0.82    -- -103.00 -69.00-142.30   50
 51  \w   -100.00 -75.00   0.50    0.82    -- -103.00 -75.00 159.23   50
 52  \w   -173.00-114.00   0.50    0.82    -- -103.00 -77.00  90.00  118
 53  \w   -103.00 -78.00   0.50    0.82    -- -103.00 -68.00 130.43   50
 54  \w   -165.00-139.00   0.50    0.82    -- -103.00 -64.00 112.63   52
 55  \w   -105.00 -77.00   0.50    0.82    -- -103.00 -71.00  70.57   56
 56  \w   -104.00 -74.00   0.50    0.82    -- -103.00 -77.00 -60.00   60
 57  \w   -104.00 -78.00   0.50    0.82    -- -103.00 -70.00-118.03   52
 58  \w   -137.00-111.00   0.50    0.82    -- -103.00 -77.00 -60.00   52
 59  \w   -173.00-126.00   0.50    0.82    -- -103.00 -67.00   3.83   94
 60  \w   -173.00 -74.00   0.50    0.82    -- -103.00 -77.00  22.31  198
 61  \w   -172.00 -74.00   0.50    0.82    -- -103.00 -77.00  60.00  196
 62  \w   -105.00 -80.00   0.50    0.82    -- -103.00 -61.00  30.00   50
 63  \w    -99.00 -74.00   0.50    0.82    -- -103.00 -77.00-120.00   50
 64  \w   -102.00 -77.00   0.50    0.82    -- -103.00 -69.00  -7.92   50
 65  \w   -100.00 -75.00   0.50    0.82    -- -103.00 -74.00 -81.53   50
 66  \w   -171.00 -74.00   0.50    0.82    -- -103.00 -77.00 -90.00  194
 67  \w   -167.00 -74.00   0.50    0.82    -- -103.00 -77.00 -46.83  186
 68  \w    -64.00 -29.00   0.50    0.82    -- -103.00  61.00 120.00   70
 69  \w     38.00  99.00   0.50    0.82    --  108.16 -77.00  60.00  122
 70  \w     73.00 106.00   0.50    0.82    --  108.16 -95.00-180.00   66
 71  \w     37.00 112.00   0.50    0.82    --  108.16-125.00   0.00  150
 72  \w     41.00 104.00   0.50    0.82    --  108.16 -77.00-150.00  126
 73  \w     39.00  65.00   0.50    0.82    --  108.16 -95.00-180.00   52
 74  \w     34.00 103.00   0.50    0.82    --  108.16 -95.00  60.00  138
 75  \w     47.00 111.00   0.50    0.82    --  108.16-125.00  30.00  128
 76  \w     42.00 111.00   0.50    0.82    --  108.16-125.00-150.00  138
 77  \w     81.00 106.00   0.50    0.82    --  108.16 -77.00 -30.00   50
 78  \w     48.00  78.00   0.50    0.82    --  108.16 -77.00 -30.00   60
 79  \w     81.00 112.00   0.50    0.82    --  108.16-125.00-180.00   62
 80  \w     48.00  73.00   0.50    0.82    --  108.16-125.00-180.00   50
 81  \w     40.00  93.00   0.50    0.82    --  108.16-125.00 -30.00  106
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            33435
_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         75.374
_diffrn_reflns_theta_min         3.812
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.116a (Rigaku Oxford Diffraction, 2024)
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    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_preparation       'slow evaporation'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0405P)^2^+0.5150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2849
_reflns_number_total             3001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt02523k2.cif
_cod_data_source_block           pd-cs-sb-698-carb_auto
_cod_depositor_comments
'Adding full bibliography for 7719798--7719801.cif.'
_cod_database_code               7719801
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         ' C H N '
_cell_oxdiff_angle_alpha         89.9966(14)
_cell_oxdiff_angle_beta          102.1469(12)
_cell_oxdiff_angle_gamma         90.0163(12)
_cell_oxdiff_length_a            11.86039(14)
_cell_oxdiff_length_b            17.1462(3)
_cell_oxdiff_length_c            7.42484(13)
_cell_oxdiff_measurement_reflns_used 21435
_cell_oxdiff_volume              1476.11(4)
_shelx_estimated_absorpt_t_max   0.886
_shelx_estimated_absorpt_t_min   0.859
_diffrn_oxdiff_digest_hkl
;
43a9177b05c7c15becdae3d2c616593f21d194
;
_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
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C008(H008), C009(H009), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00J), C00J(H00K), C00K(H00L),
 C00L(H00M), C00M(H00N)
2.b Idealised Me refined as rotating group:
 C00H(H00A,H00H,H00I)
;
_shelx_res_checksum              10482
_shelx_hkl_checksum              50088
_olex2_exptl_crystal_mounting_method 'mitegen loop'
_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 1.464
_oxdiff_exptl_absorpt_empirical_full_min 0.713