Nitroso-dienophile additions to dendralenes: a short synthesis of branched aminosugars.
Wang, Ruomeng; Bojase, Gomotsang; Willis, Anthony C.; Paddon-Row, Michael N; Sherburn, Michael S.; Organic letters 14 (2012) 5652–5655; doi:10.1021/ol302619r

data_1508737
_publ_section_title
;
 Nitroso-dienophile additions to dendralenes: a short synthesis of
 branched aminosugars.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5652
_journal_page_last               5655
_journal_paper_doi               10.1021/ol302619r
_journal_volume                  14
_journal_year                    2012
_chemical_compound_source        local
_chemical_formula_moiety         'C28 H27 N3 O3'
_chemical_formula_sum            'C28 H27 N3 O3'
_chemical_formula_weight         453.54
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             12-07-10
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2012-07-10 - Report on C28 H27 N3 O3
             by Anthony C. Willis
             for (Cynthia) Ruomeng Wang and Mick Sherburn
2012-07-10 - passes checkcif tests with minor warnings
;
_cell_angle_alpha                105.781(3)
_cell_angle_beta                 100.075(4)
_cell_angle_gamma                115.216(4)
_cell_formula_units_Z            2
_cell_length_a                   9.9709(6)
_cell_length_b                   10.7612(9)
_cell_length_c                   13.1112(11)
_cell_measurement_reflns_used    43817
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1154.44(17)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_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      200
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.072
_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       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25708
_diffrn_reflns_theta_full        27.525
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         2.847
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480.000
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.51
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9562
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5284
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.0003226
_refine_ls_shift/su_mean         0.0000769
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.47P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1429
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1429
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3152
_reflns_number_total             5284
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.55
_oxford_diffrn_Wilson_scale      1.83
_oxford_refine_ls_r_factor_ref   0.1054
_oxford_refine_ls_scale          0.782(2)
_oxford_reflns_number_all        5284
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '7101057 she1222a'
_cod_data_source_file            ol302619r_si_006.cif
_cod_data_source_block           she1222a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_cell_volume        1154.43(17)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               1508737
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, O(1,U'S) UNTIL C(34) 
CONT O(120,U'S,OCC) O(20,OCC) N(121,U'S,OCC) N(21,OCC) 
EQUIV O(20,OCC) O(120,OCC) N(21,OCC) N(121,OCC) 
WEIGHT -1 O(120,OCC) N(121,OCC) 
EQUIV N(21,U[11]) N(121,U[11]) 
EQUIV N(21,U[22]) N(121,U[22]) 
EQUIV N(21,U[33]) N(121,U[33]) 
EQUIV N(21,U[12]) N(121,U[12]) 
EQUIV N(21,U[13]) N(121,U[13]) 
EQUIV N(21,U[23]) N(121,U[23]) 
RIDE C   (   3,X'S) H   (  31,X'S) H   (  32,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  62,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H( 191,X'S) H( 192,X'S) H(193,X'S) H(194,X'S) 
RIDE C   (  22,X'S) H( 221,X'S) H( 222,X'S) H(223,X'S) H(224,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,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   (  34,X'S) H   ( 341,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
DIST 1.427, .02 = C(19) TO O(120) 
DIST 1.456, .02 = O(120) TO N(121) 
DIST 1.422, .02 = N(121) TO C(23) 
DIST 1.467, .02 = N(121) TO C(22) 
REM 
VIBR 0.0, .01 = C(19) TO O(120) 
VIBR 0.0, .01 = O(120) TO N(121) 
VIBR 0.0, .01 = N(121) TO C(23), N(121) TO C(22) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;