Diastereoselective Synthesis of (±)-<i>epi</i>-Subincanadine C.
Kalshetti, Manojkumar G.; Argade, Narshinha P.; ACS omega 3 (2018) 5308–5316; doi:10.1021/acsomega.8b00587

data_4515970
_publ_section_title
;
 Diastereoselective Synthesis of (+-)-<i>epi</i>-Subincanadine C.
;
_journal_issue                   5
_journal_name_full               'ACS omega'
_journal_page_first              5308
_journal_page_last               5316
_journal_paper_doi               10.1021/acsomega.8b00587
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C22 H26 N2 O'
_chemical_formula_sum            'C22 H26 N2 O'
_chemical_formula_weight         334.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2018-04-26
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.646(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8071(17)
_cell_length_b                   23.863(6)
_cell_length_c                   11.839(3)
_cell_measurement_reflns_used    2251
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.91
_cell_measurement_theta_min      2.48
_cell_volume                     1842.5(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9897
_diffrn_measured_fraction_theta_max 0.9897
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14843
_diffrn_reflns_theta_full        25.3896
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         1.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0690 before and 0.0462 after correction. The Ratio of minimum to maximum transmission is 0.9571. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2056
_exptl_crystal_description       block
_exptl_crystal_F_000             720.2828
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.2433
_refine_diff_density_min         -0.2651
_refine_diff_density_rms         0.0579
_refine_ls_d_res_high            0.8288
_refine_ls_d_res_low             11.9316
_refine_ls_goodness_of_fit_ref   1.0451
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0451
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+0.3749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -8
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2556
_reflns_number_total             3360
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ao8b00587_si_002.cif
_cod_data_source_block           mo_NM_06_0ma
_cod_database_code               4515970
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00a,H00c), C00E(H00g,H00h), C00I(H00k,H00l)
2.c Aromatic/amide H refined with riding coordinates:
 N002(H002), C00F(H00i), C00G(H00j), C00J(H00m), C00K(H00n), C00L(H00o),
 C00M(H00p)
2.d Idealised Me refined as rotating group:
 C00D(H00d,H00e,H00f), C00N(H00q,H00r,H00s), C00O(H00t,H00u,H00v), C00P(H00w,
 H00x,H00y)
;
_olex2_submission_special_instructions 'No special instructions were received'