One-Pot Asymmetric Synthesis of Alkylidene 1-Alkylindan-1-ols Using Brønsted Acid and Palladium Catalysis.
Faggyas, Réka J; Calder, Ewen D. D.; Wilson, Claire; Sutherland, Andrew; The Journal of organic chemistry 82 (2017) 11585–11593; doi:10.1021/acs.joc.7b02287

data_4032986
_publ_section_title
;
 One-Pot Asymmetric Synthesis of Alkylidene 1-Alkylindan-1-ols Using
 Br\/onsted Acid and Palladium Catalysis.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11585
_journal_page_last               11593
_journal_paper_doi               10.1021/acs.joc.7b02287
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C14 H19 N O2'
_chemical_formula_sum            'C14 H19 N O2'
_chemical_formula_weight         233.30
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   7.7296(3)
_cell_length_b                   7.7296(3)
_cell_length_c                   18.3472(9)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    290
_cell_measurement_theta_max      67.69
_cell_measurement_theta_min      6.61
_cell_volume                     949.32(7)
_computing_cell_refinement       'SAINT V8.37A (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.9-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'APEX3 Ver. 2016.9-0 (Bruker-AXS, 2016)'
_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_temperature      290
_diffrn_detector                 'charge integrating pixel array detector'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10651
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.685
_diffrn_reflns_theta_min         6.613
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'INCOATEC I\ms 3.0'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1616 before and 0.0546 after correction. The Ratio 
of minimum to maximum transmission is 0.9221. The \l/2 correction 
factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       block
_exptl_crystal_F_000             378
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.103
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
;
 Flack x determined using 1061 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2237
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0510P)^2^+0.1050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0801
_reflns_Friedel_coverage         0.981
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                2214
_reflns_number_total             2237
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02287_si_003.cif
_cod_data_source_block           cu_2017gu0019_0m
_cod_depositor_comments
'Adding full bibliography for 4032985--4032986.cif.'
_cod_original_cell_volume        949.32(9)
_cod_database_code               4032986
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.777
_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:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6"(H6"A,H6"B), C2"(H2"A,H2"B), C2(H2A,H2B), C5"(H5"A,H5"B), C3"(H3"A,H3"B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              1256
_shelx_hkl_checksum              76963
_olex2_submission_special_instructions 'No special instructions were received'