Overcoming Synthetic Challenges of Oridonin A-Ring Structural Diversification: Regio- and Stereoselective Installation of Azides and 1,2,3-Triazoles at the C-1, C-2, or C-3 Position
Ding, Chunyong; Zhang, Yusong; Chen, Haijun; Wild, Christopher; Wang, Tianzhi; White, Mark A.; Shen, Qiang; Zhou, Jia; Organic Letters 15 (2013) 3718–; doi:10.1021/ol4015865

data_1512195
_publ_section_title
;
 Overcoming Synthetic Challenges of Oridonin A-Ring Structural
 Diversification: Regio- and Stereoselective Installation of Azides and
 1,2,3-Triazoles at the C-1, C-2, or C-3 Position
;
_journal_issue                   14
_journal_name_full               'Organic Letters'
_journal_page_first              3718
_journal_paper_doi               10.1021/ol4015865
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_compound_source        'Chemical Synthesis'
_chemical_formula_moiety         'C28 H31 N3 O5, C O'
_chemical_formula_sum            'C29 H31 N3 O6'
_chemical_formula_weight         517.57
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 92.814(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2382(6)
_cell_length_b                   13.1872(11)
_cell_length_c                   15.8280(14)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    263
_cell_measurement_theta_max      67
_cell_measurement_theta_min      3
_cell_volume                     1300.5(2)
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_data_reduction        'SAINT (Siemens ,1995)'
_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      263
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10230
_diffrn_reflns_theta_max         66.677
_diffrn_reflns_theta_min         4.366
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       hornblende
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.24
_refine_ls_abs_structure_details 'Flack (1983), 1945 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       31(12)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9847
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.0007296
_refine_ls_shift/su_mean         0.0000714
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.08P)^2^ + 0.16P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1201
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1201
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3946
_reflns_number_total             4272
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.96
_oxford_diffrn_Wilson_scale      1.47
_oxford_refine_ls_r_factor_ref   0.0472
_oxford_refine_ls_scale          0.855(4)
_oxford_reflns_number_all        4241
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            ol4015865_si_003.cif
_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 2.4.2 from
2011-04-26.

'_atom_sites_solution_primary' value 'Direct' changed to
'direct' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               1512195
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
CONT ENANTIO 
RIDE O   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE O   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE O   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  17,X'S) H   ( 172,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  19,X'S) H   ( 192,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) H   ( 352,X'S) H   ( 353,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 363,X'S) H   ( 362,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;