trans-Selective and Switchable Arene Hydrogenation of Phenol Derivatives
Wollenburg, Marco; Heusler, Arne; Bergander, Klaus; Glorius, Frank; ACS Catalysis 10 (2020) 11365–11370; doi:10.1021/acscatal.0c03423

data_4518051
_publ_section_title
;
 trans-Selective and Switchable Arene Hydrogenation of Phenol Derivatives
;
_journal_issue                   19
_journal_name_full               'ACS Catalysis'
_journal_page_first              11365
_journal_page_last               11370
_journal_paper_doi               10.1021/acscatal.0c03423
_journal_volume                  10
_journal_year                    2020
_chemical_formula_sum            'C11 H21 N O3'
_chemical_formula_weight         215.29
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'APEX3 v2016.1-0'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8601(3)
_cell_length_b                   5.6544(2)
_cell_length_c                   44.1243(15)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      69.1964
_cell_measurement_theta_min      4.0075
_cell_volume                     2460.06(14)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            33803
_diffrn_reflns_theta_full        69.27
_diffrn_reflns_theta_max         69.27
_diffrn_reflns_theta_min         4.01
_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.215
_refine_ls_abs_structure_details
;

Flack x determined using 1777 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4551
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0572
_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^)+3.5147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                4145
_reflns_number_total             4551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03423_si_002.cif
_cod_data_source_block           glo9616
_cod_depositor_comments
'Adding full bibliography for 4518051--4518054.cif.'
_cod_database_code               4518051
_shelx_res_checksum              71143
_shelx_hkl_checksum              92575