Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol
Aciro, Caroline; Davies, Stephen G.; Roberts, Paul M.; Russell, Angela J.; Smith, Andrew D.; Thomson, James E.; Organic & Biomolecular Chemistry 6 (2008) 3762–3770; doi:10.1039/b808812h

data_7150993
_publ_section_title
;
 Ammonium-directed dihydroxylation: metal-free synthesis of the
 diastereoisomers of 3-aminocyclohexane-1,2-diol
;
_journal_issue                   20
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              3762
_journal_page_last               3770
_journal_paper_doi               10.1039/b808812h
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C20 H25 N1 O2'
_chemical_formula_sum            'C20 H25 N O2'
_chemical_formula_weight         311.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 110.5571(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.83920(10)
_cell_length_b                   28.0222(3)
_cell_length_c                   12.21180(10)
_cell_measurement_reflns_used    8039
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     3473.00(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15636
_diffrn_reflns_theta_full        26.990
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         5.145
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1211
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         4662
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.000525
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.262 0.921E-01 0.701E-01
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0861
_refine_ls_wR_factor_gt          0.0459
_refine_ls_wR_factor_ref         0.0426
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              36
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                5130
_reflns_number_total             7908
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.78
_oxford_diffrn_Wilson_scale      13.10
_oxford_refine_ls_r_factor_ref   0.0403
_oxford_refine_ls_scale          0.2869(4)
_oxford_reflns_number_all        7908
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            b808812h.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 1 21/a 1 '
_cod_original_formula_sum        'C20 H25 N1 O2'
_cod_database_code               7150993