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_4035080
_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         'C22 H28 Cl3 N1 O3'
_chemical_formula_sum            'C22 H28 Cl3 N O3'
_chemical_formula_weight         460.83
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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                 91.810(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1718(12)
_cell_length_b                   8.9442(8)
_cell_length_c                   19.711(2)
_cell_measurement_reflns_used    1725
_cell_measurement_temperature    150
_cell_measurement_theta_max      75
_cell_measurement_theta_min      4
_cell_volume                     1087.5(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 0.987
_diffrn_measured_fraction_theta_max 0.559
_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     1.54180
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2978
_diffrn_reflns_theta_full        25.221
_diffrn_reflns_theta_max         76.429
_diffrn_reflns_theta_min         2.243
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.009
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.24
_refine_ls_abs_structure_details 'Flack (1983), 735 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.08(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2020
_refine_ls_number_restraints     181
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.0002104
_refine_ls_shift/su_mean         0.0000072
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 2.30P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1248
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1248
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              7
_reflns_limit_k_min              -11
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                1927
_reflns_number_total             2097
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.29
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0506
_oxford_refine_ls_scale          10.2(6)
_oxford_reflns_number_all        2020
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE O   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  11,X'S) H   ( 111,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   (  17,X'S) H   ( 173,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE O   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) 
RIDE C   (  27,X'S) H   ( 272,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE O   (  29,X'S) H   ( 291,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.08000 = CL(1) TO C(2) 
U(IJ) .0, 0.08000 = C(2) TO CL(3) 
U(IJ) .0, 0.08000 = C(2) TO CL(4) 
U(IJ) .0, 0.08000 = O(5) TO C(6) 
U(IJ) .0, 0.04000 = C(6) TO C(7) 
U(IJ) .0, 0.04000 = C(6) TO C(28) 
U(IJ) .0, 0.04000 = C(7) TO N(8) 
U(IJ) .0, 0.04000 = C(7) TO C(24) 
U(IJ) .0, 0.04000 = N(8) TO C(9) 
U(IJ) .0, 0.04000 = N(8) TO C(16) 
U(IJ) .0, 0.04000 = C(9) TO C(10) 
U(IJ) .0, 0.04000 = C(10) TO C(11) 
U(IJ) .0, 0.04000 = C(10) TO C(15) 
U(IJ) .0, 0.04000 = C(11) TO C(12) 
U(IJ) .0, 0.04000 = C(12) TO C(13) 
U(IJ) .0, 0.04000 = C(13) TO C(14) 
U(IJ) .0, 0.04000 = C(14) TO C(15) 
U(IJ) .0, 0.08000 = C(16) TO C(17) 
U(IJ) .0, 0.04000 = C(16) TO C(18) 
U(IJ) .0, 0.04000 = C(18) TO C(19) 
U(IJ) .0, 0.04000 = C(18) TO C(23) 
U(IJ) .0, 0.04000 = C(19) TO C(20) 
U(IJ) .0, 0.04000 = C(20) TO C(21) 
U(IJ) .0, 0.04000 = C(21) TO C(22) 
U(IJ) .0, 0.04000 = C(22) TO C(23) 
U(IJ) .0, 0.08000 = C(24) TO O(25) 
U(IJ) .0, 0.04000 = C(24) TO C(26) 
U(IJ) .0, 0.04000 = C(26) TO C(27) 
U(IJ) .0, 0.04000 = C(27) TO C(28) 
U(IJ) .0, 0.08000 = C(28) TO O(29) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            jo8b01359_si_002.cif
_cod_data_source_block           28
_cod_original_cell_volume        1087.6(3)
_cod_original_formula_sum        'C22 H28 Cl3 N1 O3'
_cod_database_code               4035080