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_7122442
_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_absolute_configuration ad
_chemical_formula_moiety         'C14 H14 O3'
_chemical_formula_sum            'C14 H14 O3'
_chemical_formula_weight         230.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-06-05
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.9951(5)
_cell_length_b                   14.2011(3)
_cell_length_c                   6.89980(10)
_cell_measurement_reflns_used    3461
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.1790
_cell_measurement_theta_min      6.2290
_cell_volume                     2351.15(8)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_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    -50.00  30.00   1.00   17.50    --  -43.08  38.00-180.00   80
  2  \w     29.00 103.00   1.00   17.50    --   43.08-134.00-108.00   74
  3  \w      6.00 122.00   1.00   17.50    --   43.08  19.00 -90.00  116
  4  \w     25.00 109.00   1.00   70.00    --  106.43 -94.00-150.00   84
  5  \w     32.00  91.00   1.00   70.00    --  106.43 -30.00-150.00   59
  6  \w     32.00  91.00   1.00   70.00    --  106.43 -30.00-120.00   59
  7  \w     35.00  98.00   1.00   70.00    --  106.43 -45.00-180.00   63
  8  \w     35.00  90.00   1.00   70.00    --  106.43 -45.00 -60.00   55
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas 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      0.0287012000
_diffrn_orient_matrix_UB_12      0.0594805000
_diffrn_orient_matrix_UB_13      -0.0595272000
_diffrn_orient_matrix_UB_21      -0.1046116000
_diffrn_orient_matrix_UB_22      0.0161338000
_diffrn_orient_matrix_UB_23      -0.0185355000
_diffrn_orient_matrix_UB_31      -0.0009931000
_diffrn_orient_matrix_UB_32      0.0179530000
_diffrn_orient_matrix_UB_33      0.2144389000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8261
_diffrn_reflns_point_group_measured_fraction_full 0.709
_diffrn_reflns_point_group_measured_fraction_max 0.673
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.603
_diffrn_reflns_theta_min         3.617
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.813
_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    1.301
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_recrystallization_method
'crystallised from a mixture of diethyl ether and n-pentane'
_exptl_crystal_size_max          0.706
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3250
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0534P)^2^+0.3148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0957
_reflns_Friedel_coverage         0.274
_reflns_Friedel_fraction_full    0.362
_reflns_Friedel_fraction_max     0.317
_reflns_number_gt                2917
_reflns_number_total             3250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc06388e2.cif
_cod_data_source_block           hphwlc
_cod_depositor_comments
'Adding full bibliography for 7122441--7122443.cif.'
_cod_database_code               7122442
_nottingham_internal_coll_name   HPHWLC
_nottingham_internal_coll_number 17704
_nottingham_internal_coll_client HP/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '70.00, 17.50'
_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 'GVB, PL13110001'
_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 5/6/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 5/6/2018
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H14 O3'
_chemical_oxdiff_usercomment
'HPHWLC #17704 GVB-1517 IN FOMBLIN ON MICROMOUNT FOR HP/HWL'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.2(3)
 -0.2(3)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C35(H35A,H35B), C36(H36A,H36B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C25(H25), C26(H26), C27(H27), C28(H28)
3.c X=CH2 refined with riding coordinates:
 C17(H17A,H17B), C37(H37A,H37B)
3.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              99078
_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 HP738
_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 1.803
_oxdiff_exptl_absorpt_empirical_full_min 0.734