Total synthesis of atropodiastereomers of heterodimeric <i>Amaryllidaceae</i> alkaloids: narcipavline and narcikachnine.
Pal, Souvik; Majumder, Satyajit; Niyogi, Sovan; Shyamal, Pranay; Mondal, Debabrata; Das, Bishnu; Bisai, Alakesh; Chemical science 15 (2024) 19851–19857; doi:10.1039/d4sc04361h

data_1573066
_publ_section_title
;
 Total synthesis of atropodiastereomers of heterodimeric
 <i>Amaryllidaceae</i> alkaloids: narcipavline and narcikachnine.
;
_journal_issue                   47
_journal_name_full               'Chemical science'
_journal_page_first              19851
_journal_page_last               19857
_journal_paper_doi               10.1039/d4sc04361h
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C33 H32 N2 O5, C3 H8 O'
_chemical_formula_sum            'C36 H40 N2 O6'
_chemical_formula_weight         596.70
_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'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc2kbwd6
_audit_creation_date             2024-06-05
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-06-19 deposited with the CCDC.	2024-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.134(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5497(2)
_cell_length_b                   13.3748(3)
_cell_length_c                   19.9348(3)
_cell_measurement_reflns_used    19900
_cell_measurement_temperature    100.00(16)
_cell_measurement_theta_max      67.5660
_cell_measurement_theta_min      3.8850
_cell_volume                     3021.47(10)
_computing_cell_refinement       'CrysAlisPro 1.171.43.119a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.119a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.119a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -111.00 -30.00   0.50    2.94    --  -40.83 160.00-177.00  162
  2  \w    -84.00  -7.00   0.50    2.94    --  -40.83 118.00  30.00  154
  3  \w   -110.00 -49.00   0.50    2.94    --  -40.83-160.00 152.00  122
  4  \w     51.00 113.00   0.50    2.94    --   40.83-160.00 152.00  124
  5  \w     51.00 113.00   0.50    2.94    --   40.83-160.00 152.00  124
  6  \w   -143.00 -49.00   0.50   11.74    --  -82.50-160.00 152.00  188
  7  \w   -143.00 -49.00   0.50   11.74    --  -82.50-160.00 152.00  188
  8  \w   -146.00 -77.00   0.50   11.74    --  -82.50-118.00 -55.00  138
  9  \w     33.00 110.00   0.50   11.74    --   96.35-118.00 -55.00  154
 10  \w     71.00 159.00   0.50   11.74    --   96.35 160.00-177.00  176
 11  \w     51.00 136.00   0.50   11.74    --   96.35-160.00 152.00  170
 12  \w     51.00 136.00   0.50   11.74    --   96.35-160.00 152.00  170
 13  \w   -108.00 -63.00   0.50    2.94    --  -40.83-139.00 -90.00   90
 14  \w    -28.00  31.00   0.50    2.94    --  -40.83  21.00 -60.00  118
 15  \w    -37.00  27.00   0.50    2.94    --  -40.83  32.00  30.00  128
 16  \w   -108.00 -63.00   0.50    2.94    --  -40.83-139.00 -30.00   90
 17  \w     17.00 110.00   0.50    2.94    --   40.83  66.00-150.00  186
 18  \w    -35.00  24.00   0.50    2.94    --   40.83 -11.00 -60.00  118
 19  \w     17.00 110.00   0.50    2.94    --   40.83  66.00  30.00  186
 20  \w     18.00  78.00   0.50    2.94    --   40.83-104.00-150.00  120
 21  \w     17.00 110.00   0.50    2.94    --   40.83  66.00  30.00  186
 22  \w     17.00 110.00   0.50    2.94    --   40.83  66.00-150.00  186
 23  \w     29.00  84.00   0.50    2.94    --   40.83-118.00 -55.00  110
 24  \w   -150.00 -66.00   0.50   11.74    --  -82.50 -42.00-150.00  168
 25  \w    -85.00 -19.00   0.50   11.74    --  -82.50 118.00  30.00  132
 26  \w    -47.00 -15.00   0.50   11.74    --  -82.50  42.00   0.00   64
 27  \w    -47.00 -15.00   0.50   11.74    --  -82.50  42.00  60.00   64
 28  \w    105.00 170.00   0.50   11.74    --   96.35  96.00 -30.00  130
 29  \w     33.00 110.00   0.50   11.74    --   96.35-117.00 120.00  154
 30  \w     29.00  83.00   0.50   11.74    --   96.35 -68.00 -60.00  108
 31  \w     75.00 165.00   0.50   11.74    --   96.35  59.00-150.00  180
 32  \w     75.00 165.00   0.50   11.74    --   96.35  59.00-150.00  180
 33  \w     23.00 106.00   0.50   11.74    --   96.35 -96.00 120.00  166
 34  \w     28.00  68.00   0.50   11.74    --   96.35 -59.00 -30.00   80
 35  \w     23.00 106.00   0.50   11.74    --   96.35 -96.00 120.00  166
 36  \w     83.00 164.00   0.50   11.74    --   96.35  33.00 150.00  162
 37  \w     30.00  57.00   0.50   11.74    --   96.35 -50.00 120.00   54
 38  \w     44.00 127.00   0.50   11.74    --   96.35-145.00 -60.00  166
 39  \w     30.00  57.00   0.50   11.74    --   96.35 -50.00   0.00   54
 40  \w     33.00 110.00   0.50   11.74    --   96.35-117.00 -30.00  154
 41  \w     30.00  57.00   0.50   11.74    --   96.35 -50.00-180.00   54
 42  \w     99.00 160.00   0.50   11.74    --   96.35 117.00 -60.00  122
 43  \w    105.00 170.00   0.50   11.74    --   96.35  96.00 -90.00  130
 44  \w    105.00 170.00   0.50   11.74    --   96.35  96.00-120.00  130
 45  \w     99.00 160.00   0.50   11.74    --   96.35 118.00  30.00  122
 46  \w   -109.00 -14.00   0.50    2.94    --  -40.83 -77.00  90.00  190
 47  \w    -28.00  31.00   0.50    2.94    --  -40.83  21.00-120.00  118
 48  \w   -109.00 -14.00   0.50    2.94    --  -40.83 -77.00 -30.00  190
 49  \w   -109.00 -14.00   0.50    2.94    --  -40.83 -77.00 150.00  190
 50  \w   -109.00 -14.00   0.50    2.94    --  -40.83 -77.00  30.00  190
 51  \w   -108.00 -63.00   0.50    2.94    --  -40.83-139.00  30.00   90
 52  \w     28.00 109.00   0.50    2.94    --   40.83  32.00 -30.00  162
 53  \w     14.00 110.00   0.50    2.94    --   40.83  77.00 -30.00  192
 54  \w     17.00 110.00   0.50    2.94    --   40.83  66.00 150.00  186
 55  \w     17.00 110.00   0.50    2.94    --   40.83  66.00-120.00  186
 56  \w     14.00 110.00   0.50    2.94    --   40.83  77.00 -90.00  192
 57  \w     24.00 108.00   0.50    2.94    --   40.83  43.00 120.00  168
 58  \w     77.00 162.00   0.50   11.74    --   96.35  50.00  90.00  170
 59  \w     83.00 164.00   0.50   11.74    --   96.35  33.00  30.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            43284
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.329
_diffrn_reflns_theta_min         3.901
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52797
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.119a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         5477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0829P)^2^+1.8346P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1595
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4506
_reflns_number_total             5477
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04361h2.cif
_cod_data_source_block           ab_sp_dhnpv_auto
_cod_depositor_comments
'Adding full bibliography for 1573064--1573066.cif.'
_cod_database_code               1573066
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C00M(H00M), C00Y(H00Y), C016(H016)
1.b Secondary CH2 refined with riding coordinates:
 C00Q(H00B,H00C), C00T(H00D,H00E), C00U(H00F,H00G), C00V(H00H,H00I), C00W(H00J,
 H00L), C015(H01G,H01H)
1.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00K(H00K), C00N(H00N), C00O(H00O), C00P(H00P), C00R(H00R),
 C00S(H00S), C00Z(H00Z), C010(H010), C013(H013), C014(H014)
1.d Idealised Me refined as rotating group:
 C011(H01A,H01B,H01C), C012(H01D,H01E,H01F), C017(H01I,H01J,H01K), C018(H01L,
 H01M,H01N)
1.e Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_shelx_res_checksum              30838
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;