Diastereoselective Ammonium-Directed Epoxidation in the Asymmetric Syntheses of Dihydroconduramines (+)-C-2, (-)-C-2, (+)-D-2, (+)-E-2, (+)-F-2, and (-)-F-2.
Da Silva Pinto, Solange; Davies, Stephen G.; Fletcher, Ai M.; Roberts, Paul M.; Thomson, James E.; The Journal of organic chemistry 83 (2018) 9939–9957; doi:10.1021/acs.joc.8b01359

data_4035082
_publ_section_title
;
 Diastereoselective Ammonium-Directed Epoxidation in the Asymmetric
 Syntheses of Dihydroconduramines (+)-C-2, (-)-C-2, (+)-D-2, (+)-E-2,
 (+)-F-2, and (-)-F-2.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9939
_journal_page_last               9957
_journal_paper_doi               10.1021/acs.joc.8b01359
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H27 N1 O3'
_chemical_formula_sum            'C21 H27 N O3'
_chemical_formula_weight         341.45
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.15836(7)
_cell_length_b                   10.69592(12)
_cell_length_c                   24.2138(2)
_cell_measurement_reflns_used    18948
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     1853.94(3)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            38280
_diffrn_reflns_theta_full        76.298
_diffrn_reflns_theta_max         76.298
_diffrn_reflns_theta_min         3.651
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details 'Flack (1983), 1631 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.03(15)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0015
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3596
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.0003971
_refine_ls_shift/su_mean         0.0000549
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.31P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0795
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0794
_reflns_limit_h_max              9
_reflns_limit_h_min              -8
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                3516
_reflns_number_total             3873
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.61
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0307
_oxford_refine_ls_scale          7.16(16)
_oxford_reflns_number_all        3597
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            jo8b01359_si_002.cif
_cod_data_source_block           42
_cod_original_cell_volume        1853.93(3)
_cod_original_formula_sum        'C21 H27 N1 O3'
_cod_database_code               4035082
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
EQUIV PART (1001,OCC) PART (1002, OCC) 
WEIGHT -1 PART (1002,OCC) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
PLANAR C(12) C(130) C(140) C(150) C(160) C(170) C(180) 
PLANAR C(12) C(131) C(141) C(151) C(161) C(171) C(181) 
VIB 0, .002 = C(190) TO C(12) 
CONT C(12) TO C(130) 
CONT C(130) TO C(140) 
CONT C(140) TO C(150) 
CONT C(150) TO C(160) 
CONT C(160) TO C(170) 
CONT C(170) TO C(180) 
CONT C(180) TO C(130) 
VIB 0, .002 = C(191) TO C(12) 
CONT C(12) TO C(131) 
CONT C(131) TO C(141) 
CONT C(141) TO C(151) 
CONT C(151) TO C(161) 
CONT C(161) TO C(171) 
CONT C(171) TO C(181) 
CONT C(181) TO C(131) 
U(IJ) 0, .01 = C(190) TO C(12) 
CONT C(12) TO C(130) 
CONT C(130) TO C(140) 
CONT C(140) TO C(150) 
CONT C(150) TO C(160) 
CONT C(160) TO C(170) 
CONT C(170) TO C(180) 
CONT C(180) TO C(130) 
U(IJ) 0, .01 = C(191) TO C(12) 
CONT C(12) TO C(131) 
CONT C(131) TO C(141) 
CONT C(141) TO C(151) 
CONT C(151) TO C(161) 
CONT C(161) TO C(171) 
CONT C(171) TO C(181) 
CONT C(181) TO C(131) 
DIST 0, 0.1 = MEAN C(130) TO C(140) 
CONT C(140) TO C(150) 
CONT C(150) TO C(160) 
CONT C(160) TO C(170) 
CONT C(170) TO C(180) 
CONT C(180) TO C(130) 
DIST 0, 0.1 = MEAN C(131) TO C(141) 
CONT C(141) TO C(151) 
CONT C(151) TO C(161) 
CONT C(161) TO C(171) 
CONT C(171) TO C(181) 
CONT C(181) TO C(131) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;