2,2'-dihydroxybenzil: a stereodynamic probe for primary amines controlled by steric strain.
Seo, Min-Seob; Lee, Ansoo; Kim, Hyunwoo; Organic letters 16 (2014) 2950–2953; doi:10.1021/ol501088v

data_1516050
_publ_section_title
;
 2,2'-dihydroxybenzil: a stereodynamic probe for primary amines controlled
 by steric strain.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2950
_journal_page_last               2953
_journal_paper_doi               10.1021/ol501088v
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H36 N2 O2'
_chemical_formula_sum            'C26 H36 N2 O2'
_chemical_formula_weight         408.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5434(6)
_cell_length_b                   11.5090(6)
_cell_length_c                   19.6411(10)
_cell_measurement_reflns_used    9517
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      66.68
_cell_measurement_theta_min      4.45
_cell_volume                     2383.3(2)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            42204
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.686
_diffrn_reflns_theta_min         4.453
_diffrn_source                   'ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.7064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.105
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 1757 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       0.0038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0238
_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^)+(0.0319P)^2^+0.3224P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0625
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                4135
_reflns_number_total             4141
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol501088v_si_002.cif
_cod_data_source_block           d13148
_cod_depositor_comments          'Adding full bibliography for 1516050.cif.'
_cod_database_code               1516050
_shelx_estimated_absorpt_t_min   0.804
_shelx_estimated_absorpt_t_max   0.883
_shelxl_version_number           2013-3