Syntheses of Dihydroconduramines (±)-B-1, (±)-E-1, and (±)-F-1 via Diastereoselective Epoxidation of N-Protected 4-Aminocyclohex-2-en-1-ols.
Brennan, Méabh B; Csatayová, Kristína; Davies, Stephen G.; Fletcher, Ai M.; Green, William D.; Lee, James A.; Roberts, Paul M.; Russell, Angela J.; Thomson, James E.; The Journal of organic chemistry 80 (2015) 6609–6618; doi:10.1021/acs.joc.5b00716

data_4031121
_publ_section_title
;
 Syntheses of Dihydroconduramines (+-)-B-1, (+-)-E-1, and (+-)-F-1 via
 Diastereoselective Epoxidation of N-Protected 4-Aminocyclohex-2-en-1-ols.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6609
_journal_page_last               6618
_journal_paper_doi               10.1021/acs.joc.5b00716
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C20 H21 N1 O2'
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.39
_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   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 111.0571(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1751(2)
_cell_length_b                   9.85900(10)
_cell_length_c                   14.8593(2)
_cell_measurement_reflns_used    4003
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1664.52(4)
_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    '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 0.991
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.013
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6758
_diffrn_reflns_theta_full        26.939
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         5.326
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_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    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.58
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0803
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3788
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.1012
_refine_ls_shift/su_max          0.0002047
_refine_ls_shift/su_mean         0.0000189
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.01P)^2^ + 6.42P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2218
_refine_ls_wR_factor_gt          0.2207
_refine_ls_wR_factor_ref         0.2218
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3561
_reflns_number_total             3788
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.60
_oxford_diffrn_Wilson_scale      0.81
_oxford_refine_ls_r_factor_ref   0.1044
_oxford_refine_ls_scale          1.18(1)
_oxford_reflns_number_all        3788
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            jo5b00716_si_002.cif
_cod_data_source_block           34
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/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
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4031119--4031122.cif.
;
_cod_original_formula_sum        'C20 H21 N1 O2'
_cod_database_code               4031121
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   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   (  10,X'S) H   ( 101,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) H   ( 152,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,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   ( 230,X'S) H   (2302,X'S) H   (2301,X'S) 
RIDE C   ( 231,X'S) H   (2311,X'S) 
RIDE C   ( 300,X'S) H   (3002,X'S) H   (3001,X'S) 
RIDE C   ( 301,X'S) H   (3011,X'S) 
RIDE O   ( 100,X'S) H   (5000,X'S) 
RIDE O   ( 102,X'S) H   (5001,X'S) 
EQUIV PART (1001,OCC) PART (1002, OCC) 
WEIGHT -1 PART (1002,OCC) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
VIB 0, .002 = C(5) TO O(4) 
CONT O(4) TO C(301) 
CONT C(5) TO C(301) 
CONT C(301) TO C(2) 
CONT C(2) TO O(100) 
CONT C(2) TO C(230) 
CONT C(22) TO O(24) 
CONT C(22) TO C(231) 
CONT O(24) TO C(231) 
CONT C(231) TO C(2) 
CONT C(2) TO O(101) 
CONT C(2) TO C(300) 
U(IJ) 0, .01 = C(5) TO O(4) 
CONT O(4) TO C(301) 
CONT C(5) TO C(301) 
CONT C(301) TO C(2) 
CONT C(2) TO O(100) 
CONT C(2) TO C(230) 
CONT C(22) TO O(24) 
CONT C(22) TO C(231) 
CONT O(24) TO C(231) 
CONT C(231) TO C(2) 
CONT C(2) TO O(101) 
CONT C(2) TO C(300) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;