Synthesis of tricyclic nitrogen heterocycles by a sequence of palladium-catalyzed N-H and C(sp3)-H arylations.
Guyonnet, Mathieu; Baudoin, Olivier; Organic letters 14 (2012) 398–401; doi:10.1021/ol2031763

data_1503568
_publ_section_title
;
 Synthesis of tricyclic nitrogen heterocycles by a sequence of
 palladium-catalyzed N-H and C(sp3)-H arylations.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              398
_journal_page_last               401
_journal_paper_doi               10.1021/ol2031763
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C15 H17 N O4'
_chemical_formula_sum            'C15 H17 N O4'
_chemical_formula_weight         275.30
_space_group_IT_number           14
_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
_cell_angle_alpha                90
_cell_angle_beta                 114.76(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8860(10)
_cell_length_b                   21.928(3)
_cell_length_c                   8.2920(10)
_cell_measurement_reflns_used    5719
_cell_measurement_temperature    110
_cell_measurement_theta_max      29.5066
_cell_measurement_theta_min      3.3902
_cell_volume                     1302.1(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            41610
_diffrn_reflns_theta_full        25.105
_diffrn_reflns_theta_max         29.535
_diffrn_reflns_theta_min         3.398
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.221
_refine_diff_density_max         0.70
_refine_diff_density_min         -0.97
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9851
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0874
_refine_ls_shift/su_max          0.0002197
_refine_ls_shift/su_mean         0.0000258
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.841E+04 0.130E+05 0.705E+04 0.188E+04 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1519
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1519
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                2673
_reflns_number_total             3391
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.10
_oxford_diffrn_Wilson_scale      0.06
_oxford_refine_ls_r_factor_ref   0.1042
_oxford_refine_ls_scale          13.7(7)
_oxford_reflns_number_all        3391
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            ol2031763_si_001.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Direct' changed to 'direct'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               1503568
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) H   ( 203,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
U(IJ)'S  0.0, 0.010000 = C(16) TO O(20) 
U(IJ)'S  0.0, 0.010000 = O(17) TO O(2) 
END                                                                             
;