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_7122443
_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         'C16 H17 N O3'
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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                   18.5434(6)
_cell_length_b                   8.2224(3)
_cell_length_c                   18.7134(7)
_cell_measurement_reflns_used    3755
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.3160
_cell_measurement_theta_min      4.7700
_cell_volume                     2853.26(18)
_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      '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 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_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    -65.00  28.00   1.00    1.00    --  -38.50  77.00  90.00   93
  2  \w    -31.00   7.00   1.00    1.00    --  -38.50  77.00 -30.00   38
  3  \w     90.00 158.00   1.00    1.00    --  106.13  77.00-180.00   68
  4  \w    153.00 178.00   1.00    1.00    --  106.13  77.00  90.00   25
  5  \w    145.00 177.00   1.00    1.00    --  106.13  77.00  60.00   32
  6  \w     80.00 174.00   1.00    1.00    --  106.13  77.00 -60.00   94
  7  \w    115.00 173.00   1.00    1.00    --  106.13  77.00 150.00   58
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_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      0.0359593000
_diffrn_orient_matrix_UB_12      0.1176085000
_diffrn_orient_matrix_UB_13      0.0532396000
_diffrn_orient_matrix_UB_21      -0.0441166000
_diffrn_orient_matrix_UB_22      -0.0755975000
_diffrn_orient_matrix_UB_23      0.0614135000
_diffrn_orient_matrix_UB_31      0.0604968000
_diffrn_orient_matrix_UB_32      -0.1247635000
_diffrn_orient_matrix_UB_33      0.0131340000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_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       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6948
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.493
_diffrn_reflns_theta_min         4.770
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.491
_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    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether'
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.293
_exptl_crystal_size_min          0.175
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+0.8197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2541
_reflns_number_total             2841
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc06388e2.cif
_cod_data_source_block           snkhld
_cod_depositor_comments
'Adding full bibliography for 7122441--7122443.cif.'
_cod_original_cell_volume        2853.25(18)
_cod_database_code               7122443
_nottingham_internal_coll_name   SNKHLD
_nottingham_internal_coll_number 17705
_nottingham_internal_coll_client SNK/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time 1.00
_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 'SN, XDA 017-09'
_nottingham_internal_process_date 04/06/2018
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 04/06/2018
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 04/06/2018
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 05/06/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 05/06/2018
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H17 N O3'
_chemical_oxdiff_usercomment
'SNKHLD #17705 SN-1333 IN FOMBLIN FILM ON A MICROMOUNT FOR SNK/HWL'
_shelx_estimated_absorpt_t_max   0.886
_shelx_estimated_absorpt_t_min   0.790
_reflns_odcompleteness_completeness 99.90
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C14 \\sim C15 \\sim C15A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
3. Others
 Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14(H14C,H14D), C16(H16A,H16B)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
4.c X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
4.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C15A(H15D,H15E,H15F)
;
_shelx_res_checksum              1097
_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 SNK-6-46
_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 1.167
_oxdiff_exptl_absorpt_empirical_full_min 0.883