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_7158493
_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         'C13 H12 N2 O2'
_chemical_formula_sum            'C13 H12 N2 O2'
_chemical_formula_weight         228.25
_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   geom
_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                 90.211(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7052(8)
_cell_length_b                   5.0360(2)
_cell_length_c                   13.3544(6)
_cell_measurement_reflns_used    4020
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      75.3350
_cell_measurement_theta_min      5.6320
_cell_volume                     1056.21(8)
_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      99.9(5)
_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     24.00 120.00   0.50    0.27    --   46.98  77.00 -30.00  192
  2  \w    106.00 138.00   0.50    1.06    --  103.64 178.00-180.00   64
  3  \w     60.00  94.00   0.50    1.06    --  103.64 178.00-180.00   68
  4  \w     84.00 173.00   0.50    1.06    --  103.64  45.00  30.00  178
  5  \w     77.00 123.00   0.50    1.06    --  103.64 -61.00  30.00   92
  6  \w     34.00  64.00   0.50    1.06    --  103.64 -61.00  30.00   60
  7  \w    -88.00 -11.00   0.50    1.06    --  -90.25 111.00  30.00  154
  8  \w   -105.00 -15.00   0.50    1.06    --  -90.25  77.00 -90.00  180
  9  \w    -72.00 -16.00   0.50    0.27    --  -46.98  77.00 -90.00  112
 10  \w     27.00  68.00   0.50    1.06    --  103.64 -15.00 150.00   82
 11  \w     86.00 113.00   0.50    1.06    --  103.64-111.00 150.00   54
 12  \w     35.00 112.00   0.50    1.06    --  103.64-111.00   0.00  154
 13  \w     46.00 103.00   0.50    1.06    --  103.64 -95.00   0.00  114
 14  \w     69.00 104.00   0.50    1.06    --  103.64-111.00 -60.00   70
 15  \w     32.00  58.00   0.50    1.06    --  103.64-111.00-180.00   52
 16  \w     73.00 111.00   0.50    1.06    --  103.64-111.00-180.00   76
 17  \w     42.00  68.00   0.50    0.27    --   46.98-125.00 -90.00   52
 18  \w     42.00  98.00   0.50    0.27    --   46.98-125.00  60.00  112
 19  \w     87.00 131.00   0.50    1.06    --  103.64 -15.00 150.00   88
 20  \w   -103.00 -22.00   0.50    0.27    --  -46.98 -77.00  60.00  162
 21  \w   -159.00 -70.00   0.50    1.06    --  -90.25 -61.00 150.00  178
 22  \w   -158.00-109.00   0.50    1.06    --  -90.25 -45.00 -30.00   98
 23  \w   -155.00-128.00   0.50    1.06    --  -90.25 -45.00-150.00   54
 24  \w   -158.00 -70.00   0.50    1.06    --  -90.25 -61.00-180.00  176
 25  \w   -106.00 -79.00   0.50    1.06    --  -90.25 -45.00-150.00   54
 26  \w     38.00  63.00   0.50    1.06    --  103.64-111.00 -90.00   50
 27  \w     64.00  90.00   0.50    1.06    --  103.64 -95.00 -60.00   52
 28  \w     30.00  60.00   0.50    1.06    --  103.64-111.00 150.00   60
;
_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      0.0235429000
_diffrn_orient_matrix_UB_12      -0.2349835000
_diffrn_orient_matrix_UB_13      0.0685224000
_diffrn_orient_matrix_UB_21      -0.0856472000
_diffrn_orient_matrix_UB_22      -0.1339949000
_diffrn_orient_matrix_UB_23      -0.0252539000
_diffrn_orient_matrix_UB_31      0.0417670000
_diffrn_orient_matrix_UB_32      -0.1425481000
_diffrn_orient_matrix_UB_33      -0.0892805000
_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  0.0308
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8761
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.718
_diffrn_reflns_theta_min         5.634
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77944
_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    1.435
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0910P)^2^+0.8516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1545
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1785
_reflns_number_total             1894
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02372a2.cif
_cod_data_source_block           jl3_12b
_cod_depositor_comments
'Adding full bibliography for 7158492--7158494.cif.'
_cod_database_code               7158493
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C13H12N2O2
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.882
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.62
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_shelx_res_checksum              54733
_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 1.354
_oxdiff_exptl_absorpt_empirical_full_min 0.755