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_1573064
_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         'C17 H19 N O4'
_chemical_formula_sum            'C17 H19 N O4'
_chemical_formula_weight         301.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2jb7kp
_audit_creation_date             2024-02-18
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-18 deposited with the CCDC.	2024-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.393(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7354(2)
_cell_length_b                   15.3138(2)
_cell_length_c                   9.9359(2)
_cell_measurement_reflns_used    13575
_cell_measurement_temperature    100.01(15)
_cell_measurement_theta_max      68.0000
_cell_measurement_theta_min      2.8180
_cell_volume                     1428.17(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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    -98.00 -20.00   0.50    0.22    --  -40.58 140.00  44.00  156
  2  \w    -90.00 -15.00   0.50    0.22    --  -40.58 130.00-128.00  150
  3  \w     42.00 101.00   0.50    0.22    --   40.58-140.00 -13.00  118
  4  \w     37.00  93.00   0.50    0.22    --   40.58-130.00 159.00  112
  5  \w   -150.00 -63.00   0.50    0.86    --  -82.50-140.00 -13.00  174
  6  \w   -148.00 -69.00   0.50    0.86    --  -82.50-130.00 159.00  158
  7  \w    -98.00 -20.00   0.50    0.86    --  -82.50 140.00  44.00  156
  8  \w     37.00 116.00   0.50    0.86    --   96.35-130.00 159.00  158
  9  \w     42.00 124.00   0.50    0.86    --   96.35-140.00 -13.00  164
 10  \w     84.00 164.00   0.50    0.86    --   96.35 140.00  44.00  160
 11  \w    -24.00  35.00   0.50    0.22    --  -40.58  12.00 -90.00  118
 12  \w    -31.00  30.00   0.50    0.22    --  -40.58  25.00   0.00  122
 13  \w   -107.00 -21.00   0.50    0.22    --  -40.58 -50.00 150.00  172
 14  \w    -24.00  35.00   0.50    0.22    --  -40.58  12.00 -60.00  118
 15  \w    -35.00  24.00   0.50    0.22    --   40.58 -12.00-150.00  118
 16  \w    -29.00  31.00   0.50    0.22    --   40.58 -25.00 150.00  120
 17  \w    -35.00  24.00   0.50    0.22    --   40.58 -12.00-120.00  118
 18  \w   -146.00 -78.00   0.50    0.86    --  -82.50-117.00 120.00  136
 19  \w    -47.00 -15.00   0.50    0.86    --  -82.50  42.00 120.00   64
 20  \w    -68.00 -14.00   0.50    0.86    --  -82.50  59.00-150.00  108
 21  \w    -47.00 -15.00   0.50    0.86    --  -82.50  42.00  90.00   64
 22  \w     30.00  57.00   0.50    0.86    --   96.35 -50.00 -90.00   54
 23  \w     28.00 105.00   0.50    0.86    --   96.35 -77.00-180.00  154
 24  \w     30.00  57.00   0.50    0.86    --   96.35 -50.00  30.00   54
 25  \w     30.00  57.00   0.50    0.86    --   96.35 -50.00 -30.00   54
 26  \w     83.00 164.00   0.50    0.86    --   96.35  33.00-150.00  162
 27  \w     33.00 110.00   0.50    0.86    --   96.35-117.00-150.00  154
 28  \w     71.00 170.00   0.50    0.86    --   96.35  17.00-180.00  198
 29  \w     33.00 110.00   0.50    0.86    --   96.35-117.00-180.00  154
 30  \w     29.00  83.00   0.50    0.86    --   96.35 -68.00 120.00  108
 31  \w     30.00  57.00   0.50    0.86    --   96.35 -50.00-180.00   54
 32  \w     81.00 165.00   0.50    0.86    --   96.35 145.00   0.00  168
 33  \w     28.00  68.00   0.50    0.86    --   96.35 -59.00-120.00   80
 34  \w    105.00 170.00   0.50    0.86    --   96.35  96.00  90.00  130
 35  \w    105.00 170.00   0.50    0.86    --   96.35  96.00 120.00  130
 36  \w   -108.00 -17.00   0.50    0.22    --  -40.58 -64.00  60.00  182
 37  \w   -108.00 -17.00   0.50    0.22    --  -40.58 -64.00 120.00  182
 38  \w   -109.00 -14.00   0.50    0.22    --  -40.58 -77.00  30.00  190
 39  \w   -107.00 -25.00   0.50    0.22    --  -40.58 -38.00 -60.00  164
 40  \w   -109.00 -14.00   0.50    0.22    --  -40.58 -77.00 -60.00  190
 41  \w   -109.00 -14.00   0.50    0.22    --  -40.58 -77.00-150.00  190
 42  \w   -109.00 -14.00   0.50    0.22    --  -40.58 -77.00-120.00  190
 43  \w   -108.00 -17.00   0.50    0.22    --  -40.58 -64.00 -90.00  182
 44  \w    -67.00  28.00   0.50    0.22    --  -40.58  77.00 120.00  190
 45  \w   -109.00 -14.00   0.50    0.22    --  -40.58 -77.00   0.00  190
 46  \w   -151.00 -61.00   0.50    0.86    --  -82.50 -59.00  60.00  180
 47  \w   -150.00 -58.00   0.50    0.86    --  -82.50 -68.00 -30.00  184
 48  \w   -151.00 -55.00   0.50    0.86    --  -82.50 -77.00 120.00  192
 49  \w   -150.00 -58.00   0.50    0.86    --  -82.50 -68.00  30.00  184
 50  \w     29.00  83.00   0.50    0.86    --   96.35 -68.00   0.00  108
 51  \w     72.00 164.00   0.50    0.86    --   96.35  68.00-120.00  184
 52  \w     80.00 164.00   0.50    0.86    --   96.35  42.00 -60.00  168
 53  \w     81.00 167.00   0.50    0.86    --   96.35  25.00   0.00  172
 54  \w     70.00 165.00   0.50    0.86    --   96.35  77.00 150.00  190
 55  \w     23.00 106.00   0.50    0.86    --   96.35 -96.00   0.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0227941000
_diffrn_orient_matrix_UB_12      -0.0966986000
_diffrn_orient_matrix_UB_13      -0.0429180000
_diffrn_orient_matrix_UB_21      0.1009739000
_diffrn_orient_matrix_UB_22      -0.0273401000
_diffrn_orient_matrix_UB_23      0.1410377000
_diffrn_orient_matrix_UB_31      -0.1274181000
_diffrn_orient_matrix_UB_32      -0.0043854000
_diffrn_orient_matrix_UB_33      0.0643064000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20564
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_min         5.447
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brownish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0558P)^2^+0.5406P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1028
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2347
_reflns_number_total             2597
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04361h2.cif
_cod_data_source_block           ab_aya_sp02261br_auto
_cod_depositor_comments
'Adding full bibliography for 1573064--1573066.cif.'
_cod_database_code               1573064
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     LT
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C13(H13), C2(H2)
1.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C1(H1A,H1B), C9(H9A,H9B)
1.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C4(H4), C3(H3)
1.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C17(H17A,H17B,H17C)
1.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              33593
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.769
_oxdiff_exptl_absorpt_empirical_full_min 0.579