Catalytic Cross-Coupling of Secondary Alcohols.
Thiyagarajan, Subramanian; Gunanathan, Chidambaram; Journal of the American Chemical Society 141 (2019) 3822–3827; doi:10.1021/jacs.9b00025

data_4128510
_publ_section_title
;
 Catalytic Cross-Coupling of Secondary Alcohols.
;
_journal_issue                   9
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3822
_journal_page_last               3827
_journal_paper_doi               10.1021/jacs.9b00025
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         '4(C22 H26 O2)'
_chemical_formula_sum            'C88 H104 O8'
_chemical_formula_weight         1289.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-09
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.175(4)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   18.4511(8)
_cell_length_b                   7.8907(2)
_cell_length_c                   13.3139(4)
_cell_measurement_reflns_used    6594
_cell_measurement_temperature    294.8(3)
_cell_measurement_theta_max      75.6660
_cell_measurement_theta_min      6.1480
_cell_volume                     1841.69(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.8(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.970
_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    -55.00  -7.00   0.50    4.00    --    0.00 133.00 111.00   96
  2  \w    -56.00  -9.00   0.50    4.00    --    0.00 136.00 -71.00   94
  3  \w     40.00 123.00   0.50   16.00    --  102.08-133.00  42.00  166
  4  \w     41.00 126.00   0.50   16.00    --  102.08-136.00-134.00  170
  5  \w     88.00 164.00   0.50   16.00    --  102.08 136.00 -71.00  152
  6  \w     90.00 164.00   0.50   16.00    --  102.08 133.00 111.00  148
  7  \w     -1.00  65.00   0.50    4.00    --    0.00  37.00-120.00  132
  8  \w     -1.00  65.00   0.50    4.00    --    0.00  37.00-150.00  132
  9  \w     -1.00  67.00   0.50    4.00    --    0.00  19.00  90.00  136
 10  \w     39.00 105.00   0.50   16.00    --  102.08 -45.00 -30.00  132
 11  \w     39.00 118.00   0.50   16.00    --  102.08-125.00   0.00  158
 12  \w     36.00 103.00   0.50   16.00    --  102.08 -30.00   0.00  134
 13  \w     34.00 108.00   0.50   16.00    --  102.08 -94.00  60.00  148
 14  \w     35.00 104.00   0.50   16.00    --  102.08 -15.00 -30.00  138
 15  \w    101.00 164.00   0.50   16.00    --  102.08  77.00 -90.00  126
 16  \w    102.00 127.00   0.50   16.00    --  102.08  30.00   0.00   50
 17  \w    133.00 168.00   0.50   16.00    --  102.08  30.00   0.00   70
 18  \w    108.00 142.00   0.50   16.00    --  102.08 125.00  30.00   68
 19  \w     39.00 101.00   0.50   16.00    --  102.08 -45.00-180.00  124
 20  \w     69.00  97.00   0.50   16.00    --  102.08 -45.00-150.00   56
 21  \w    129.00 154.00   0.50   16.00    --  102.08  45.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0197557000
_diffrn_orient_matrix_UB_12      0.1770894000
_diffrn_orient_matrix_UB_13      0.0327885000
_diffrn_orient_matrix_UB_21      -0.0855954000
_diffrn_orient_matrix_UB_22      -0.0418454000
_diffrn_orient_matrix_UB_23      -0.0447753000
_diffrn_orient_matrix_UB_31      0.0013942000
_diffrn_orient_matrix_UB_32      -0.0707516000
_diffrn_orient_matrix_UB_33      0.1084335000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1227
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12166
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.487
_diffrn_reflns_theta_min         5.046
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.439
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.439
_refine_ls_R_factor_all          0.1686
_refine_ls_R_factor_gt           0.1433
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3234
_refine_ls_wR_factor_ref         0.3537
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2741
_reflns_number_total             3641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b00025_si_002.cif
_cod_data_source_block           cg-stn-736
_cod_database_code               4128510
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C84 H88 O8 '
_diffrn_oxdiff_ac3_digest_frames
;
01d534d88b8b8a1c6d93827e16c3338a830002710f8
;
_diffrn_oxdiff_ac3_digest_hkl
;
012d93a2b23b67aa3874643f4f968790c7938f
;
_reflns_odcompleteness_completeness 98.42
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C16(H16A,H16B), C4(H4A,H4B), C6(H6A,H6B), C3(H3A,H3B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15), C22(H22), C18(H18), C21(H21),
 C20(H20), C19(H19)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 9.171
_oxdiff_exptl_absorpt_empirical_full_min 0.240