Acridine-based copper(I) PNP pincer complexes: catalysts for alkyne hydroboration and borylation of aryl halides.
Olding, Angus; Lucas, Nigel T.; Ho, Curtis C.; Bissember, Alex C.; Dalton transactions (Cambridge, England : 2003) 53 (2024) 4471–4478; doi:10.1039/d3dt04269c

data_7715127
_publ_section_title
;
 Acridine-based copper(I) PNP pincer complexes: catalysts for alkyne
 hydroboration and borylation of aryl halides.
;
_journal_issue                   10
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4471
_journal_page_last               4478
_journal_paper_doi               10.1039/d3dt04269c
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         '1.999(C39 H55 Br Cu N P2), C H2 Cl2'
_chemical_formula_sum            'C78.97 H112 Br2 Cl2 Cu2 N2 P4'
_chemical_formula_weight         1571.08
_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
_audit_creation_date             2024-01-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-01-23 deposited with the CCDC.	2024-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.2960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.08470(10)
_cell_length_b                   31.6404(4)
_cell_length_c                   22.2392(3)
_cell_measurement_reflns_used    23964
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.6260
_cell_measurement_theta_min      3.9270
_cell_volume                     7793.57(16)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3449
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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 -37.00   1.00    2.50    --  -42.04 178.00 -60.00   85
  2  \w    -44.00  31.00   1.00    2.50    --  -42.04  57.00-150.00   75
  3  \w    -51.00 -21.00   1.00    2.50    --  -42.04 -38.00  60.00   30
  4  \w    -94.00 -29.00   1.00    2.50    --  -42.04 -57.00-120.00   65
  5  \w   -101.00 -18.00   1.00    2.50    --  -42.04 -38.00  30.00   83
  6  \w     39.00  73.00   1.00    2.50    --   42.04 -99.00-120.00   34
  7  \w     38.00  72.00   1.00   12.50    --  104.32 -61.00 -90.00   34
  8  \w     33.00 132.00   1.00   12.50    --  104.32 -30.00 150.00   99
  9  \w     23.00 106.00   1.00   12.50    --  104.32 -95.00   0.00   83
 10  \w     48.00 106.00   1.00   12.50    --  104.32 -95.00 -90.00   58
 11  \w    143.00 178.00   1.00   12.50    --  104.32  77.00 -60.00   35
 12  \w     61.00 130.00   1.00   12.50    --  104.32 -45.00 -60.00   69
 13  \w     34.00 101.00   1.00   12.50    --  104.32 -95.00 150.00   67
 14  \w     47.00 106.00   1.00   12.50    --  104.32 -95.00-150.00   59
 15  \w    129.00 154.00   1.00   12.50    --  104.32  77.00  60.00   25
 16  \w    110.00 175.00   1.00   12.50    --  104.32  77.00-120.00   65
 17  \w     30.00 103.00   1.00   12.50    --  104.32 -95.00  90.00   73
 18  \w     18.00 171.00   1.00   12.50    --  104.32   0.00-120.00  153
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1168176000
_diffrn_orient_matrix_UB_12      0.0075687000
_diffrn_orient_matrix_UB_13      -0.0336669000
_diffrn_orient_matrix_UB_21      0.0237106000
_diffrn_orient_matrix_UB_22      -0.0479745000
_diffrn_orient_matrix_UB_23      -0.0008316000
_diffrn_orient_matrix_UB_31      -0.0716476000
_diffrn_orient_matrix_UB_32      -0.0035605000
_diffrn_orient_matrix_UB_33      -0.0605962000
_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  0.0416
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            58282
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.737
_diffrn_reflns_theta_min         3.429
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.596
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.484
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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            'light orange'
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       needle
_exptl_crystal_F_000             3287
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.620
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     830
_refine_ls_number_reflns         15277
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+5.0840P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12830
_reflns_number_total             15277
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt04269c2.cif
_cod_data_source_block           compound_1b
_cod_depositor_comments
'Adding full bibliography for 7715123--7715127.cif.'
_cod_database_code               7715127
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C39 H55 Br1 Cu1 N1 P2'
_chemical_oxdiff_usercomment     'M604 NTL acb_AO-7-133B'
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.433
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C105) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
3. Rigid body (RIGU) restrains
 C106, C105, C91, C92
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C105
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: H10E(0.75) H10F(0.75) H10G(0.25) H10H(0.25) C105(0.75) H10I(0.75)
 H10J(0.75) H10K(0.75) H10L(0.75) H10M(0.25) H10N(0.25) C16(0.25) H16A(0.25)
 H16B(0.25)
5.a Ternary CH refined with riding coordinates:
 C21(H21), C27(H27), C41(H41), C47(H47), C81(H81), C87(H87), C101(H101),
 C107(H107)
5.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,
 H24B), C25(H25A,H25B), C26(H26A,H26B), C28(H28A,H28B), C29(H29A,H29B),
 C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C42(H42A,H42B), C43(H43A,H43B),
  C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B), C48(H48A,H48B), C49(H49A,
 H49B), C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B), C74(H74A,H74B),
 C75(H75A,H75B), C82(H82A,H82B), C83(H83A,H83B), C84(H84A,H84B), C85(H85A,H85B),
  C86(H86A,H86B), C88(H88A,H88B), C89(H89A,H89B), C90(H90A,H90B), C91(H91A,
 H91B), C92(H92A,H92B), C102(H10A,H10B), C103(H10C,H10D), C104(H10E,H10F),
 C104(H10G,H10H), C105(H10I,H10J), C106(H10K,H10L), C106(H10M,H10N), C108(H10O,
 H10P), C109(H10Q,H10R), C110(H11A,H11B), C111(H11C,H11D), C112(H11E,H11F),
 C201(H20A,H20B), C16(H16A,H16B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C62(H62), C63(H63),
 C64(H64), C65(H65), C66(H66), C67(H67), C68(H68)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              3668
_shelx_fab_checksum              93751
_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 1.354
_oxdiff_exptl_absorpt_empirical_full_min 0.819