Palladium-catalyzed ortho-acylation of 2-aryl pyridine derivatives using arylmethyl amines as new acyl sources
Qian Zhang; Fan Yang; Yangjie Wu; Chem.Commun. 49 (2013) 6837–; doi:10.1039/c3cc42106f

data_7109546
_publ_section_title
;
 Palladium-catalyzed ortho-acylation of 2-aryl pyridine derivatives using
 arylmethyl amines as new acyl sources
;
_journal_name_full               Chem.Commun.
_journal_page_first              6837
_journal_paper_doi               10.1039/c3cc42106f
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C20 H17 N O'
_chemical_formula_sum            'C20 H17 N O'
_chemical_formula_weight         287.35
_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
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Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
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_cell_length_b                   10.2717(13)
_cell_length_c                   11.4612(16)
_cell_measurement_reflns_used    2759
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.3097
_cell_measurement_theta_min      3.1611
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
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_computing_structure_solution
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SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
1 omega 12.00 38.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- -17.2104 0.0000 -180.0000 26
2 omega -25.00 4.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- -17.2104 -99.0000 150.0000 29
3 omega 36.00 95.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 19.9448 178.0000 150.0000 59
4 omega -24.00 86.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 19.9448 19.0000 -150.0000 110
5 omega -53.00 -28.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
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6 omega -11.00 23.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
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7 omega -17.00 25.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- -17.1323 -99.0000 -150.0000 42
8 omega 55.00 96.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 19.8666 178.0000 60.0000 41
9 omega 24.00 50.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 19.8666 -108.0000 -154.0000 26
10 omega 7.00 91.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 19.8666 0.0000 120.0000 84
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0490062000
_diffrn_orient_matrix_UB_12      -0.0416392000
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_diffrn_orient_matrix_UB_22      -0.0584595000
_diffrn_orient_matrix_UB_23      -0.0689924000
_diffrn_orient_matrix_UB_31      0.0763060000
_diffrn_orient_matrix_UB_32      -0.0309374000
_diffrn_orient_matrix_UB_33      0.0171602000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6950
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_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         3.16
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
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_refine_ls_extinction_method     none
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_refine_ls_number_parameters     201
_refine_ls_number_reflns         3178
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_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+0.1189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                2427
_reflns_number_total             3178
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc42106f.txt
_cod_data_source_block           201112184
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        782.78(18)
_cod_database_code               7109546
_chemical_oxdiff_formula         'C11 H10 S O2'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32