Palladium-Catalyzed Ullmann Cross-Coupling/Tandem Reductive Cyclization Route to Key Members of the Uleine Alkaloid Family.
Tang, Fei; Banwell, Martin G.; Willis, Anthony C.; The Journal of organic chemistry 81 (2016) 2950–2957; doi:10.1021/acs.joc.6b00240

data_4031955
_publ_section_title
;
 Palladium-Catalyzed Ullmann Cross-Coupling/Tandem Reductive Cyclization
 Route to Key Members of the Uleine Alkaloid Family.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2950
_journal_page_last               2957
_journal_paper_doi               10.1021/acs.joc.6b00240
_journal_volume                  81
_journal_year                    2016
_chemical_compound_source        local
_chemical_formula_moiety         'C21 H28 N2 O2'
_chemical_formula_sum            'C21 H28 N2 O2'
_chemical_formula_weight         340.47
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_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             15-11-17
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2015-11-17 - Report on C21 H28 N2 O2
            by Anthony C. Willis
            for   Xiang Ma and Martin Banwell

2015-11-17 - passes checkcif tests with minor warnings

2016-01-30 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 103.2795(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1738(2)
_cell_length_b                   10.6826(1)
_cell_length_c                   17.3464(3)
_cell_measurement_reflns_used    10793
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      5
_cell_volume                     1834.84(5)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2015)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
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_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28325
_diffrn_reflns_theta_full        72.343
_diffrn_reflns_theta_max         72.343
_diffrn_reflns_theta_min         4.629
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.090
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_refine_diff_density_max         0.22
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     None
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_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         3623
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.0006840
_refine_ls_shift/su_mean         0.0000895
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.57P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0750
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0750
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                3271
_reflns_number_total             3623
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.11
_oxford_diffrn_Wilson_scale      0.04
_oxford_refine_ls_r_factor_ref   0.0353
_oxford_refine_ls_scale          4.96(7)
_oxford_reflns_number_all        3623
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\ban1555SN\Tony_ban1555SN_data At 15:31 on'
_cod_data_source_file            jo6b00240_si_002.cif
_cod_data_source_block           ban1555SN
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4031955
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT O    (    1 ,X'S,U'S)  UNTIL C    (   21 ) 
CONT H    (    1 ,X'S)  UNTIL H    (  213 ) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;