Total synthesis of (−)-δ-lycorane
Shukla, Jyoti; Gangwar, Manoj Kumar; Koley, Dipankar; New Journal of Chemistry 47 (2023) 18900–18904; doi:10.1039/D3NJ03567K

data_7062788
_publ_section_title
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 Total synthesis of (&#x2212;)-\d-lycorane
;
_journal_issue                   41
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18900
_journal_page_last               18904
_journal_paper_doi               10.1039/D3NJ03567K
_journal_volume                  47
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H25 N O3'
_chemical_formula_sum            'C21 H25 N O3'
_chemical_formula_weight         339.44
_chemical_name_systematic        DK-CP-504
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_Int_Tables_number      1
_audit_creation_date             2022-10-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-10-01 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                108.948(3)
_cell_angle_beta                 94.920(4)
_cell_angle_gamma                93.497(4)
_cell_formula_units_Z            1
_cell_length_a                   5.8887(8)
_cell_length_b                   8.3187(12)
_cell_length_c                   9.4843(13)
_cell_measurement_reflns_used    6414
_cell_measurement_temperature    423.15
_cell_measurement_theta_max      28.40
_cell_measurement_theta_min      2.84
_cell_volume                     435.86(11)
_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      423.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9899
_diffrn_measured_fraction_theta_max 0.9778
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6414
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.84
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2931
_exptl_crystal_description       block
_exptl_crystal_F_000             182.0889
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.2111
_refine_diff_density_min         -0.2464
_refine_diff_density_rms         0.0501
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.4(6)
_refine_ls_d_res_high            0.7471
_refine_ls_d_res_low             7.1833
_refine_ls_goodness_of_fit_ref   1.0570
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    43
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4263
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.0570
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0349P)^2^+0.1133P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.959
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              12
_reflns_limit_l_min              -12
_reflns_number_gt                3925
_reflns_number_total             4263
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3nj03567k2.cif
_cod_data_source_block           DK-CP-504
_cod_depositor_comments          'Adding full bibliography for 7062788.cif.'
_cod_original_sg_symbol_Hall     ' P 1'
_cod_database_code               7062788
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C9(H9a,H9b), C11(H11a,H11b), C12(H12a,H12b), C13(H13a,H13b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C3(H3a), C21(H21), C20(H20), C19(H19), C18(H18), C17(H17)
2.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_original_sample_id DK-CP-504
_olex2_submission_special_instructions 'No special instructions were received'