Silver-Catalyzed Long-Distance Aryl Migration from Carbon Center to Nitrogen Center.
Zhou, Taigang; Luo, Fei-Xian; Yang, Ming-Yu; Shi, Zhang-Jie; Journal of the American Chemical Society 137 (2015) 14586–14589; doi:10.1021/jacs.5b10267

data_4129749
_publ_section_title
;
 Silver-Catalyzed Long-Distance Aryl Migration from Carbon Center to
 Nitrogen Center.
;
_journal_issue                   46
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14586
_journal_page_last               14589
_journal_paper_doi               10.1021/jacs.5b10267
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C18 H15 F6 N O4 S, C3 H7'
_chemical_formula_sum            'C21 H22 F6 N O4 S'
_chemical_formula_weight         498.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-03-25
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.083(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.2964(9)
_cell_length_b                   5.6535(2)
_cell_length_c                   20.5834(9)
_cell_measurement_reflns_used    3310
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      28.9930
_cell_measurement_theta_min      3.5870
_cell_volume                     2257.65(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9931
_diffrn_measured_fraction_theta_max 0.8336
_diffrn_measurement_details
;
  1 omega  -67.00   41.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -77.0000 -120.0000 108

  2 omega   36.00   99.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017 -178.0000   60.0000 63
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0023982000
_diffrn_orient_matrix_UB_12      0.0830163000
_diffrn_orient_matrix_UB_13      0.0264420000
_diffrn_orient_matrix_UB_21      -0.0364617000
_diffrn_orient_matrix_UB_22      0.0026730000
_diffrn_orient_matrix_UB_23      -0.0082295000
_diffrn_orient_matrix_UB_31      0.0010420000
_diffrn_orient_matrix_UB_32      -0.0939889000
_diffrn_orient_matrix_UB_33      0.0231062000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8713
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         3.013
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0264P)^2^+5.8989P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3365
_reflns_number_total             4402
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b10267_si_002.cif
_cod_data_source_block           exp_3196
_cod_original_cell_volume        2257.64(18)
_cod_database_code               4129749
_chemical_oxdiff_formula         'C1 H O1N1 F1 S1'
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.957
_shelxl_version_number           2013-3