Nickel-catalyzed, ligand-free, diastereoselective synthesis of 3-methyleneindan-1-ols.
Panchal, Heena; Clarke, Christopher; Bell, Charles; Karad, Somnath Narayan; Lewis, William; Lam, Hon Wai; Chemical communications (Cambridge, England) 54 (2018) 12389–12392; doi:10.1039/c8cc06388e

data_7122441
_publ_section_title
;
 Nickel-catalyzed, ligand-free, diastereoselective synthesis of
 3-methyleneindan-1-ols.
;
_journal_issue                   87
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12389
_journal_page_last               12392
_journal_paper_doi               10.1039/c8cc06388e
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-28 deposited with the CCDC.
2018-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                95.548(3)
_cell_angle_beta                 94.576(3)
_cell_angle_gamma                92.972(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2469(3)
_cell_length_b                   9.0265(3)
_cell_length_c                   9.4627(3)
_cell_measurement_reflns_used    8027
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.9000
_cell_measurement_theta_min      4.6880
_cell_volume                     697.61(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_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     -9.00  16.00   1.00    1.00    --   32.00 102.00 132.07   25
  2  \w    -81.00  18.00   1.00    1.00    --  -42.81 102.00  61.00   99
  3  \w   -112.00 -50.00   1.00    1.00    --  -42.81 -77.00 -30.00   62
  4  \w    -46.00 -12.00   1.00    1.00    --  -42.81 -77.00 -30.00   34
  5  \w    -75.00 -20.00   1.00    1.00    --  -42.81 -38.00  30.00   55
  6  \w     24.00  91.00   1.00    1.00    --   42.81-125.00   0.00   67
  7  \w     64.00  89.00   1.00    1.00    --   42.81  57.00  90.00   25
  8  \w     21.00  46.00   1.00    1.00    --   42.81  57.00  90.00   25
  9  \w     14.00  42.00   1.00    1.00    --   44.00  79.00 169.85   28
 10  \w     18.00  45.00   1.00    1.00    --   48.00  79.00  32.29   27
 11  \w     16.00  41.00   1.00    1.00    --   48.00  81.00 -94.42   25
 12  \w     16.00  41.00   1.00    1.00    --   48.00  81.00-147.04   25
 13  \w     28.00  55.00   1.00    1.00    --   56.00  74.00 -44.31   27
 14  \w     32.00  59.00   1.00    1.00    --   60.00  75.00 122.17   27
 15  \w     96.00 123.00   1.00    1.00    --   60.00  75.00 122.17   27
 16  \w     35.00  67.00   1.00    1.00    --   64.00  77.00-101.41   32
 17  \w    107.00 136.00   1.00    1.00    --   64.00  77.00 -19.10   29
 18  \w     34.00  63.00   1.00    1.00    --   64.00  76.00-156.60   29
 19  \w     35.00  67.00   1.00    1.00    --   64.00  77.00 -19.10   32
 20  \w     34.00  72.00   1.00    1.00    --   64.00  76.00  71.44   38
 21  \w     36.00  85.00   1.00    1.00    --   64.00  77.00 139.64   49
 22  \w     96.00 134.00   1.00    1.00    --   64.00  76.00  71.44   38
 23  \w     38.00  64.00   1.00    1.00    --   68.00  76.00-146.45   26
 24  \w     38.00  70.00   1.00    1.00    --   68.00  75.00  29.06   32
 25  \w     42.00  68.00   1.00    1.00    --   72.00  75.00 -44.36   26
 26  \w     55.00 106.00   1.00    2.00    --   84.00  76.00-174.46   51
 27  \w     59.00 151.00   1.00    2.00    --   88.00  77.00  -9.61   92
 28  \w    116.00 143.00   1.00    2.00    --   96.00  67.00 -51.26   27
 29  \w     70.00 100.00   1.00    2.00    --   96.00  67.00 -51.26   30
 30  \w     26.00 110.00   1.00    2.00    --  103.32-102.00 -41.00   84
 31  \w     52.00  84.00   1.00    2.00    --  103.32 -30.00 120.00   32
 32  \w    140.00 175.00   1.00    2.00    --  103.32  77.00-150.00   35
 33  \w     73.00 100.00   1.00    2.00    --  103.32  77.00-150.00   27
 34  \w     79.00 160.00   1.00    2.00    --  103.32  61.00  90.00   81
 35  \w     74.00 175.00   1.00    2.00    --  103.32  77.00 150.00  101
 36  \w     24.00  70.00   1.00    2.00    --  103.32 -94.00   0.00   46
 37  \w    111.00 138.00   1.00    2.00    --  103.32  77.00  30.00   27
 38  \w     74.00 104.00   1.00    2.00    --  103.32  77.00  30.00   30
 39  \w     74.00 167.00   1.00    2.00    --  103.32  77.00 -90.00   93
 40  \w     33.00 117.00   1.00    2.00    --  103.32-125.00  90.00   84
 41  \w     78.00 105.00   1.00    2.00    --  103.32  77.00  90.00   27
 42  \w     79.00 145.00   1.00    2.00    --  103.32  61.00-150.00   66
 43  \w     95.00 173.00   1.00    2.00    --  103.32 125.00  30.00   78
 44  \w     78.00 143.00   1.00    2.00    --  103.32  61.00 -30.00   65
 45  \w     78.00 105.00   1.00    2.00    --  103.32  77.00   0.00   27
 46  \w    117.00 175.00   1.00    2.00    --  103.32  77.00   0.00   58
 47  \w     25.00 106.00   1.00    2.00    --  103.32 -94.00-180.00   81
 48  \w     74.00 149.00   1.00    2.00    --  103.32  77.00-120.00   75
 49  \w     86.00 113.00   1.00    2.00    --  103.32  61.00  60.00   27
 50  \w     74.00 145.00   1.00    2.00    --  103.32  77.00 120.00   71
 51  \w     34.00  89.00   1.00    2.00    --  103.32 -94.00 120.00   55
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0570468000
_diffrn_orient_matrix_UB_12      0.0604536000
_diffrn_orient_matrix_UB_13      0.1547857000
_diffrn_orient_matrix_UB_21      0.0605795000
_diffrn_orient_matrix_UB_22      -0.1539462000
_diffrn_orient_matrix_UB_23      0.0280734000
_diffrn_orient_matrix_UB_31      0.1682918000
_diffrn_orient_matrix_UB_32      0.0464259000
_diffrn_orient_matrix_UB_33      -0.0469503000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11681
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.914
_diffrn_reflns_theta_min         4.712
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.581
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether, n-pentane'
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0403P)^2^+0.1984P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2529
_reflns_number_total             2769
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc06388e2.cif
_cod_data_source_block           hphwlb
_cod_depositor_comments
'Adding full bibliography for 7122441--7122443.cif.'
_cod_original_cell_volume        697.62(4)
_cod_database_code               7122441
_nottingham_internal_coll_name   HPHWLB
_nottingham_internal_coll_number 17703
_nottingham_internal_coll_client HP/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '1.00, 2.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   24/05/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_process_date 04/06/2018
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 4/6/2018
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 4/6/2018
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 4/6/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 4/6/2018
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H16 O2'
_chemical_oxdiff_usercomment
'HPHWLB #17703 GVA-1446 MOUNTED ON MICROMOUNT IN FOMBLIN FOR HP/HWL'
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.779
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
2.c X=CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              71001
_olex2_date_sample_data_collection 2018-05-24
_olex2_date_sample_submission    2018-05-24
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id HP689
_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 1.192
_oxdiff_exptl_absorpt_empirical_full_min 0.787