Progress toward a biomimetic synthesis of pegaharmaline A.
Liyu, Jessica; Kim, Shi-Wei; Söhnel, Tilo; Sperry, Jonathan; Organic & biomolecular chemistry 20 (2022) 1275–1283; doi:10.1039/d1ob02372a

data_7158494
_publ_section_title
;
 Progress toward a biomimetic synthesis of pegaharmaline A.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1275
_journal_page_last               1283
_journal_paper_doi               10.1039/d1ob02372a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C21 H20 N4 O'
_chemical_formula_sum            'C21 H20 N4 O'
_chemical_formula_weight         344.41
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-12-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-02 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.285(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5402(3)
_cell_length_b                   7.8769(2)
_cell_length_c                   16.4206(4)
_cell_measurement_reflns_used    10013
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1340
_cell_measurement_theta_min      3.8040
_cell_volume                     1689.38(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -117.00 -49.00   0.50    0.15    --  -47.48 -74.00 144.00  136
  2  \w    -47.00   6.00   0.50    0.15    --  -47.48  74.00 -87.00  106
  3  \w    -10.00  72.00   0.50    0.15    --   47.48 -74.00 144.00  164
  4  \w   -164.00 -66.00   0.50    0.58    --  -90.25 -74.00 144.00  196
  5  \w     47.00  89.00   0.50    0.58    --  101.53 -74.00 144.00   84
  6  \w    133.00 177.00   0.50    0.58    --  101.53  74.00 -87.00   88
  7  \w     86.00 123.00   0.50    0.58    --  101.53  74.00 -87.00   74
  8  \w   -124.00 -71.00   0.50    0.15    --  -47.48-125.00  90.00  106
  9  \w   -124.00 -70.00   0.50    0.15    --  -47.48-125.00-150.00  108
 10  \w     40.00 121.00   0.50    0.15    --   47.48  57.00 -30.00  162
 11  \w    -10.00  28.00   0.50    0.15    --   47.48 -38.00 150.00   76
 12  \w    -87.00 -11.00   0.50    0.58    --  -90.25 111.00 -90.00  152
 13  \w   -153.00 -91.00   0.50    0.58    --  -90.25 -61.00   0.00  124
 14  \w   -127.00-100.00   0.50    0.58    --  -90.25 -94.00  60.00   54
 15  \w   -117.00 -71.00   0.50    0.58    --  -90.25 -30.00  30.00   92
 16  \w    -91.00 -65.00   0.50    0.58    --  -90.25  74.00 -87.00   52
 17  \w   -159.00-112.00   0.50    0.58    --  -90.25 -77.00  90.00   94
 18  \w    -82.00 -37.00   0.50    0.58    --  -90.25  61.00 120.00   90
 19  \w     86.00 174.00   0.50    0.58    --  101.53  30.00  60.00  176
 20  \w     82.00 176.00   0.50    0.58    --  101.53  45.00-120.00  188
 21  \w    124.00 172.00   0.50    0.58    --  101.53  77.00-180.00   96
 22  \w     25.00 111.00   0.50    0.58    --  101.53-111.00 120.00  172
 23  \w     82.00 110.00   0.50    0.58    --  101.53  77.00-180.00   56
 24  \w     82.00 111.00   0.50    0.58    --  101.53  30.00-150.00   58
 25  \w    129.00 176.00   0.50    0.58    --  101.53 111.00  30.00   94
 26  \w     95.00 120.00   0.50    0.58    --  101.53 -61.00  30.00   50
 27  \w     42.00  75.00   0.50    0.58    --  101.53 -61.00  30.00   66
 28  \w     25.00  90.00   0.50    0.58    --  101.53 -45.00 150.00  130
 29  \w     85.00 147.00   0.50    0.58    --  101.53  30.00   0.00  124
 30  \w     37.00 122.00   0.50    0.58    --  101.53 -61.00 150.00  170
 31  \w     91.00 158.00   0.50    0.58    --  101.53  61.00   0.00  134
 32  \w    121.00 164.00   0.50    0.58    --  101.53  30.00-150.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0521524000
_diffrn_orient_matrix_UB_12      0.1412104000
_diffrn_orient_matrix_UB_13      0.0613497000
_diffrn_orient_matrix_UB_21      0.0440204000
_diffrn_orient_matrix_UB_22      0.0765975000
_diffrn_orient_matrix_UB_23      -0.0692766000
_diffrn_orient_matrix_UB_31      -0.0962085000
_diffrn_orient_matrix_UB_32      0.1116198000
_diffrn_orient_matrix_UB_33      -0.0298339000
_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  0.0602
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19105
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.673
_diffrn_reflns_theta_max         67.673
_diffrn_reflns_theta_min         3.776
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.23a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0808P)^2^+0.5055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2822
_reflns_number_total             3053
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02372a2.cif
_cod_data_source_block           jls_37_1
_cod_depositor_comments
'Adding full bibliography for 7158492--7158494.cif.'
_cod_database_code               7158494
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H20N4O
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.967
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20), N3(H3A)
;
_shelx_res_checksum              90664
_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 1.403
_oxdiff_exptl_absorpt_empirical_full_min 0.695