Flexible Steric Bulky Bis(Imino)acenaphthene (BIAN)-Supported N-Heterocyclic Carbene Palladium Precatalysts: Catalytic Application in Buchwald-Hartwig Amination in Air.
Lan, Xiao-Bing; Li, Yinwu; Li, Yan-Fang; Shen, Dong-Sheng; Ke, Zhuofeng; Liu, Feng-Shou; The Journal of organic chemistry 82 (2017) 2914–2925; doi:10.1021/acs.joc.6b02867

data_4032421
_publ_section_title
;
 Flexible Steric Bulky Bis(Imino)acenaphthene (BIAN)-Supported
 N-Heterocyclic Carbene Palladium Precatalysts: Catalytic Application in
 Buchwald-Hartwig Amination in Air.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2914
_journal_page_last               2925
_journal_paper_doi               10.1021/acs.joc.6b02867
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C63 H54 Cl3 N3 O Pd, C H2 Cl2'
_chemical_formula_sum            'C64 H56 Cl5 N3 O Pd'
_chemical_formula_weight         1166.77
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-05-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                86.1240(10)
_cell_angle_beta                 80.0770(10)
_cell_angle_gamma                72.9690(10)
_cell_formula_units_Z            2
_cell_length_a                   12.3395(2)
_cell_length_b                   13.3565(2)
_cell_length_c                   17.8538(3)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.32
_cell_volume                     2770.94(8)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40420
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.75
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  0.9520
_exptl_absorpt_correction_T_min  0.891222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0382 before and 0.0240 after correction.
The Ratio of minimum to maximum transmission is 0.8912.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     692
_refine_ls_number_reflns         11989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0618P)^2^+2.3938P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                10390
_reflns_number_total             11989
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02867_si_002.cif
_cod_data_source_block           C3
_cod_database_code               4032421
_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. Others
 Sof(C43A)=Sof(H43D)=Sof(H43E)=Sof(H43F)=Sof(O1A)=1-FVAR(1)
 Sof(O1B)=Sof(C43B)=Sof(H43A)=Sof(H43B)=Sof(H43C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C28(H28), C46(H46), C23(H23), C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C64(H64A,H64B)
3.c Aromatic/amide H refined with riding coordinates:
 C59(H59), C10(H10), C19(H19), C6(H6), C8(H8), C9(H9), C4(H4), C41(H41),
 C30(H30), C34(H34), C20(H20), C48(H48), C61(H61), C62(H62), C52(H52), C32(H32),
  C33(H33), C37(H37), C54(H54), C50(H50), C49(H49), C58(H58), C51(H51),
 C38(H38), C55(H55), C31(H31), C39(H39), C5(H5), C57(H57), C56(H56), C44(H44),
 C40(H40), C36(H36), C63(H63), C21(H21)
3.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C18(H18A,H18B,H18C), C17(H17A,H17B,
 H17C), C43B(H43A,H43B,H43C), C43A(H43D,H43E,H43F)
;
_olex2_submission_special_instructions 'No special instructions were received'