Palladium-Catalyzed ortho-C-H Glycosylation/ipso-Alkenylation of Aryl Iodides.
Ding, Ya-Nan; Shi, Wei-Yu; Liu, Ce; Zheng, Nian; Li, Ming; An, Yang; Zhang, Zhe; Wang, Cui-Tian; Zhang, Bo-Sheng; Liang, Yong-Min; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01392

data_4038724
_publ_section_title
;
 Palladium-Catalyzed ortho-C-H Glycosylation/ipso-Alkenylation of Aryl
 Iodides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01392
_journal_year                    2020
_chemical_formula_moiety         'C23 H29 F O7'
_chemical_formula_sum            'C23 H29 F O7'
_chemical_formula_weight         436.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-12-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.321(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4240(5)
_cell_length_b                   9.53660(19)
_cell_length_c                   17.1423(5)
_cell_measurement_reflns_used    6519
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8940
_cell_measurement_theta_min      9.7140
_cell_volume                     2279.25(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -69.00  21.00   1.00    1.00    --    0.00 -57.00 150.00   90
  2  \w    -21.00  69.00   1.00    1.00    --    0.00  57.00-180.00   90
  3  \w    -72.00  26.00   1.00    1.00    --    0.00 -38.00  30.00   98
  4  \w    -15.00  75.00   1.00    1.00    --   54.00 -57.00-120.00   90
  5  \w     33.00 123.00   1.00    1.00    --   54.00  57.00 -90.00   90
  6  \w     33.00 123.00   1.00    1.00    --   54.00  57.00 120.00   90
  7  \w     33.00 123.00   1.00    1.00    --   54.00  57.00-150.00   90
  8  \w    -15.00  75.00   1.00    1.00    --   54.00 -57.00   0.00   90
  9  \w     28.00 126.00   1.00    1.00    --   54.00  38.00 150.00   98
 10  \w     23.00 111.00   1.00    1.00    --   54.00-125.00   0.00   88
 11  \w    -18.00  80.00   1.00    1.00    --   54.00 -38.00 -30.00   98
 12  \w     36.00 134.00   1.00    1.00    --  108.00 -38.00-180.00   98
 13  \w     82.00 178.00   1.00    1.00    --  108.00  38.00 -90.00   96
 14  \w     78.00 178.00   1.00    1.00    --  108.00  77.00-120.00  100
 15  \w     38.00 138.00   1.00    1.00    --  108.00 -77.00  30.00  100
 16  \w     78.00 178.00   1.00    1.00    --  108.00  77.00-180.00  100
 17  \w     85.00 176.00   1.00    1.00    --  108.00  65.00 126.00   91
 18  \w     78.00 178.00   1.00    1.00    --  108.00  77.00-150.00  100
 19  \w     78.00 178.00   1.00    1.00    --  108.00  77.00 150.00  100
 20  \w     86.00 178.00   1.00    1.00    --  108.00  50.00  30.00   92
 21  \w     82.00 178.00   1.00    1.00    --  108.00  38.00  60.00   96
 22  \w     86.00 157.00   1.00    1.00    --  108.00  63.00-120.00   71
 23  \w     52.00 131.00   1.00    1.00    --  108.00 -64.00-150.00   79
 24  \w     86.00 138.00   1.00    1.00    --  108.00  38.00  90.00   52
 25  \w     85.00 160.00   1.00    1.00    --  108.00  38.00 -60.00   75
 26  \w     81.00 166.00   1.00    1.00    --  108.00  77.00  90.00   85
 27  \w     87.00 114.00   1.00    1.00    --  108.00  50.00-120.00   27
 28  \w     92.00 176.00   1.00    1.00    --  108.00  50.00 -90.00   84
 29  \w     90.00 117.00   1.00    1.00    --  108.00  63.00-150.00   27
 30  \w     88.00 115.00   1.00    1.00    --  108.00  50.00-150.00   27
 31  \w     81.00 108.00   1.00    1.00    --  108.00  72.00-161.18   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0871664000
_diffrn_orient_matrix_UB_12      0.0618525000
_diffrn_orient_matrix_UB_13      -0.0096549000
_diffrn_orient_matrix_UB_21      0.0159454000
_diffrn_orient_matrix_UB_22      0.1041686000
_diffrn_orient_matrix_UB_23      0.0735672000
_diffrn_orient_matrix_UB_31      0.0660137000
_diffrn_orient_matrix_UB_32      -0.1068940000
_diffrn_orient_matrix_UB_33      0.0661559000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12177
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         5.621
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1579 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         4009
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0787P)^2^+0.3104P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3693
_reflns_number_total             4009
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01392_si_002.cif
_cod_data_source_block           dingyn_1217_2
_cod_database_code               4038724
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.907
_shelx_estimated_absorpt_t_min   0.845
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq, Uanis(O10) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: O5(0.7) O3AA(0.7) H0BA(0.7) H0BB(0.3) H9A(0.7) H9B(0.3) O0AA(0.75)
 H10A(0.75) H10B(0.75) H10C(0.25) H10D(0.25) C4BA(0.7) H4BA(0.7) H4BB(0.7)
 H4BC(0.7) C6AA(0.7) H6AA(0.7) H6AB(0.7) H6AC(0.7) C16(0.7) H16A(0.7) H16B(0.7)
 H16C(0.7) O1(0.25) C3AA(0.3) H3AA(0.3) H3AB(0.3) H3AC(0.3) C1(0.3) H1A(0.3)
 H1B(0.3) H1C(0.3) O7AA(0.3) O8AA(0.3) C3BA(0.3) H3BA(0.3) H3BB(0.3) H3BC(0.3)
4.a Ternary CH refined with riding coordinates:
 C6(H6), C0BA(H0BA), C0BA(H0BB), C9(H9A), C9(H9B), C1AA(H1AA), C4AA(H4AA)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10(H10C,H10D), C14(H14A,H14B)
4.c Aromatic/amide H refined with riding coordinates:
 C5AA(H5AA), C7(H7), C2(H2), C3(H3), C4(H4)
4.d Idealised Me refined as rotating group:
 C2BA(H2BA,H2BB,H2BC), C4BA(H4BA,H4BB,H4BC), C2AA(H2AA,H2AB,H2AC), C6AA(H6AA,
 H6AB,H6AC), C16(H16A,H16B,H16C), C3AA(H3AA,H3AB,H3AC), C1(H1A,H1B,H1C),
 C3BA(H3BA,H3BB,H3BC)
;
_shelx_res_checksum              20953
_shelx_hkl_checksum              7004
_olex2_date_sample_data_collection 2019-12-17
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.917
_oxdiff_exptl_absorpt_empirical_full_min 0.432