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_7158492
_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         'C23 H22 N4 O2'
_chemical_formula_sum            'C23 H22 N4 O2'
_chemical_formula_weight         386.44
_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                 102.333(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0831(2)
_cell_length_b                   9.0813(2)
_cell_length_c                   18.4230(3)
_cell_measurement_reflns_used    9085
_cell_measurement_temperature    109(2)
_cell_measurement_theta_max      74.3610
_cell_measurement_theta_min      4.0420
_cell_volume                     1974.91(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (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      109(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    104.00 132.00   0.50    0.49    --  102.39 111.00-150.00   56
  2  \w    141.00 166.00   0.50    0.49    --  102.39 111.00-150.00   50
  3  \w    100.00 164.00   0.50    0.49    --  102.39 111.00 -90.00  128
  4  \w    102.00 143.00   0.50    0.49    --  102.39 111.00 -60.00   82
  5  \w     79.00 115.00   0.50    0.49    --  102.39-111.00  60.00   72
  6  \w     63.00 109.00   0.50    0.49    --  102.39 -95.00 120.00   92
  7  \w     27.00  53.00   0.50    0.49    --  102.39-111.00  60.00   52
  8  \w      1.00  84.00   0.50    0.12    --   47.48 -99.00 150.00  166
  9  \w   -123.00 -74.00   0.50    0.12    --  -47.48-125.00 150.00   98
 10  \w   -124.00 -73.00   0.50    0.12    --  -47.48-125.00 120.00  102
 11  \w   -123.00 -70.00   0.50    0.12    --  -47.48-125.00 -60.00  106
 12  \w   -115.00 -72.00   0.50    0.12    --  -47.48-125.00-180.00   86
 13  \w   -136.00 -90.00   0.50    0.49    --  -90.25 -95.00-180.00   92
 14  \w   -141.00-116.00   0.50    0.49    --  -90.25 -59.00-141.00   50
 15  \w    -19.00  28.00   0.50    0.12    --   47.48 -59.00-141.00   94
 16  \w     55.00  99.00   0.50    0.49    --  102.39 -59.00-141.00   88
 17  \w     29.00 122.00   0.50    0.49    --  102.39 -45.00-150.00  186
 18  \w    -98.00 -73.00   0.50    0.12    --  -47.48 -59.00-141.00   50
 19  \w   -105.00 -53.00   0.50    0.49    --  -90.25  59.00  -1.00  104
 20  \w    -92.00 -66.00   0.50    0.49    --  -90.25  45.00 120.00   52
 21  \w     55.00  80.00   0.50    0.12    --   47.48  59.00  -1.00   50
 22  \w     83.00 163.00   0.50    0.49    --  102.39  30.00  90.00  160
 23  \w     81.00 173.00   0.50    0.49    --  102.39  59.00  -1.00  184
;
_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      0.1073698000
_diffrn_orient_matrix_UB_12      0.0366225000
_diffrn_orient_matrix_UB_13      0.0590166000
_diffrn_orient_matrix_UB_21      -0.0354700000
_diffrn_orient_matrix_UB_22      -0.1124738000
_diffrn_orient_matrix_UB_23      0.0533842000
_diffrn_orient_matrix_UB_31      0.0650729000
_diffrn_orient_matrix_UB_32      -0.1216776000
_diffrn_orient_matrix_UB_33      -0.0315517000
_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  0.0341
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13539
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.737
_diffrn_reflns_theta_min         6.149
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0499P)^2^+0.5149P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3170
_reflns_number_total             3567
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02372a2.cif
_cod_data_source_block           jl3_8
_cod_depositor_comments
'Adding full bibliography for 7158492--7158494.cif.'
_cod_database_code               7158492
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C23H22N4O2
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.811
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C17(H17), C20(H20), C21(H21), C22(H22),
 C23(H23), N3(H3A)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              71074
_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 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.632