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_1503569
_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_absolute_configuration ad
_chemical_formula_moiety         'C21 H20 N2 O5'
_chemical_formula_sum            'C21 H20 N2 O5'
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
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_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
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_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'light yellow'
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_exptl_crystal_description       plate
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_refine_ls_abs_structure_details 'Flack (1983), 2611 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.12(14)
_refine_ls_extinction_coef       29(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
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_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.0007897
_refine_ls_shift/su_mean         0.0000687
_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: 
 0.224E+04 0.381E+04 0.238E+04 0.102E+04 231. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1194
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_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              39
_reflns_limit_l_min              0
_reflns_number_gt                5988
_reflns_number_total             6173
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.01
_oxford_diffrn_Wilson_scale      0.09
_oxford_refine_ls_r_factor_ref   0.0442
_oxford_refine_ls_scale          3.47(5)
_oxford_reflns_number_all        6173
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            ol2031763_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_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 21 21 '
_cod_database_code               1503569
_iucr_refine_instruction_details_constraints
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BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
CONT ENANTIO 
RIDE C   (   4,X'S) H   (  42,X'S) H   (  41,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  15,X'S) H   ( 152,X'S) H   ( 151,X'S) H   ( 153,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 203,X'S) H   ( 202,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) H   ( 382,X'S) 
RIDE C   (  42,X'S) H   ( 422,X'S) H   ( 421,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) H   ( 492,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) H   ( 552,X'S) H   ( 553,X'S) 
RIDE C   (  56,X'S) H   ( 563,X'S) H   ( 562,X'S) H   ( 561,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) 
END                                                                             
;