Scope and mechanism of asymmetric C(sp3)‒H/C(Ar)‒X coupling reactions: computational and experimental study
Larionov, Evgeny; Nakanishi, Masafumi; Katayev, Dmitry; Besnard, Céline; Kündig, E. Peter; Chemical Science 4 (2013) 1995–; doi:10.1039/c3sc00098b

data_1514677
_publ_section_title
;
 Scope and mechanism of asymmetric C(sp3)--H/C(Ar)--X coupling reactions:
 computational and experimental study
;
_journal_issue                   5
_journal_name_full               'Chemical Science'
_journal_page_first              1995
_journal_paper_doi               10.1039/c3sc00098b
_journal_volume                  4
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C40 H54 I N3 O Pd'
_chemical_formula_sum            'C40 H54 I N3 O Pd'
_chemical_formula_weight         826.16
_chemical_name_systematic
;
?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2012-05-29
_audit_creation_method
;
Olex2 1.2-beta
(compiled May 9 2012 12:37:22, GUI svn.r4230)
;
_cell_angle_alpha                103.4931(16)
_cell_angle_beta                 91.2746(16)
_cell_angle_gamma                90.1766(16)
_cell_formula_units_Z            2
_cell_length_a                   11.3782(2)
_cell_length_b                   12.8716(2)
_cell_length_c                   13.5328(3)
_cell_measurement_reflns_used    29456
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.8657
_cell_measurement_theta_min      2.3344
_cell_volume                     1926.70(6)
_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
;
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
;
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
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      180
_diffrn_detector_area_resol_mean 10.4679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_details
;
1 omega -64.00 -20.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -16.8132 95.0000 -83.0000 44
2 omega -9.00 97.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 17.7507 38.0000 90.0000 106
3 omega -23.00 110.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 17.7507 77.0000 -150.0000 133
4 omega 36.00 106.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 17.7507 -178.0000 -60.0000 70
5 omega 34.00 114.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 17.7507 -178.0000 -150.0000 80
6 omega 7.00 102.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 17.7507 77.0000 -60.0000 95
7 omega -67.00 58.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 17.7507 -38.0000 -60.0000 125
8 omega -20.00 18.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -16.8132 -99.0000 -90.0000 38
9 omega -22.00 104.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 17.7507 38.0000 150.0000 126
10 omega -68.00 58.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 17.7507 -38.0000 120.0000 126
11 omega 34.00 114.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 17.7507 -178.0000 120.0000 80
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0448304000
_diffrn_orient_matrix_UB_12      0.0153437000
_diffrn_orient_matrix_UB_13      0.0379312000
_diffrn_orient_matrix_UB_21      -0.0411204000
_diffrn_orient_matrix_UB_22      0.0309614000
_diffrn_orient_matrix_UB_23      0.0328526000
_diffrn_orient_matrix_UB_31      -0.0136993000
_diffrn_orient_matrix_UB_32      -0.0449187000
_diffrn_orient_matrix_UB_33      0.0197208000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            42420
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.93
_diffrn_reflns_theta_min         2.34
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.316
_exptl_absorpt_correction_T_max  0.796
_exptl_absorpt_correction_T_min  0.662
_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_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.3725
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.2228
_refine_diff_density_max         1.205
_refine_diff_density_min         -1.477
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.026(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     854
_refine_ls_number_reflns         17934
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0265
_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^)+(0.0246P)^2^+1.0986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0596
_refine_ls_wR_factor_ref         0.0618
_reflns_number_gt                17106
_reflns_number_total             17934
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc00098b.txt
_cod_data_source_block           evmo
_cod_original_cell_volume        1926.69(6)
_cod_database_code               1514677
_chemical_oxdiff_formula         'C40 H54 I1 N3 O1 Pd1'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32