Support studies toward the hicksoane alkaloids reveal cascade reactions of a (tryptophanamido)methylglycinate.
Lee, Stephanie; Söhnel, Tilo; Sperry, Jonathan; Organic & biomolecular chemistry 21 (2023) 8708–8715; doi:10.1039/d3ob01596c

data_7159604
_publ_section_title
;
 Support studies toward the hicksoane alkaloids reveal cascade reactions
 of a (tryptophanamido)methylglycinate.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8708
_journal_page_last               8715
_journal_paper_doi               10.1039/d3ob01596c
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'Cl, C12 H14 N3 O, H O0.5'
_chemical_formula_sum            'C12 H15 Cl N3 O1.5'
_chemical_formula_weight         260.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-07-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-07-16 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.543(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4988(3)
_cell_length_b                   7.09306(15)
_cell_length_c                   13.9973(3)
_cell_measurement_reflns_used    3630
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      71.6460
_cell_measurement_theta_min      6.4680
_cell_volume                     1211.31(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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      120(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.956
_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     15.00  47.00   0.50    0.33    --   47.23 -83.00  74.00   64
  2  \w      1.00  27.00   0.50    0.33    --   47.23 -19.00 120.00   52
  3  \w     25.00  71.50   0.50    1.33    --   97.33 -61.00 150.00   93
  4  \w     73.00  99.00   0.50    1.33    --   97.33 -83.00  74.00   52
  5  \w     46.00 106.00   0.50    1.33    --   97.33 -77.00 -90.00  120
  6  \w     24.00  50.50   0.50    1.33    --   97.33 -45.00-150.00   53
  7  \w     20.00  46.50   0.50    1.33    --   97.33 -45.00-120.00   53
  8  \w     20.00  50.50   0.50    1.33    --   97.33 -45.00 -60.00   61
  9  \w     -1.00  37.00   0.50    0.33    --   47.23 -99.00-150.00   76
 10  \w     22.00  50.00   0.50    1.33    --   97.33 -45.00  60.00   56
 11  \w     21.00  51.00   0.50    1.33    --   97.33 -45.00 150.00   60
 12  \w    -33.00  -1.00   0.50    0.33    --   47.23 -19.00 120.00   64
 13  \w    -40.00   0.00   0.50    0.33    --  -47.23  38.00 120.00   80
 14  \w    -68.00 -28.00   0.50    1.33    --  -90.25  61.00 120.00   80
 15  \w    -66.00 -19.50   0.50    1.33    --  -90.25  61.00  30.00   93
 16  \w    -83.00 -33.00   0.50    1.33    --  -90.25 111.00 120.00  100
 17  \w     -2.00  26.00   0.50    0.33    --  -47.23  83.00-164.00   56
 18  \w    -37.00  -9.00   0.50    0.33    --  -47.23  83.00-164.00   56
 19  \w    -41.00 -14.50   0.50    1.33    --  -90.25 111.00-150.00   53
 20  \w    -66.00 -40.00   0.50    1.33    --  -90.25  83.00-164.00   52
 21  \w    -51.00 -15.00   0.50    1.33    --  -90.25  45.00-150.00   72
 22  \w    -78.00 -47.50   0.50    1.33    --  -90.25 111.00-150.00   61
 23  \w   -157.00 -81.00   0.50    1.33    --  -90.25 -83.00  74.00  152
 24  \w   -153.00 -83.50   0.50    1.33    --  -90.25 -95.00   0.00  139
 25  \w   -112.00 -73.50   0.50    0.33    --  -47.23-125.00-120.00   77
 26  \w    109.00 135.00   0.50    1.33    --   97.33  83.00-164.00   52
 27  \w     67.00 129.00   0.50    1.33    --   97.33 178.00-150.00  124
;
_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      0.0995991000
_diffrn_orient_matrix_UB_12      0.1332182000
_diffrn_orient_matrix_UB_13      0.0231810000
_diffrn_orient_matrix_UB_21      0.0644034000
_diffrn_orient_matrix_UB_22      -0.1349865000
_diffrn_orient_matrix_UB_23      -0.0530193000
_diffrn_orient_matrix_UB_31      -0.0433640000
_diffrn_orient_matrix_UB_32      0.1058443000
_diffrn_orient_matrix_UB_33      -0.0967520000
_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  0.0306
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4201
_diffrn_reflns_point_group_measured_fraction_full 0.842
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.156
_diffrn_reflns_theta_min         3.235
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.742
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       needle
_exptl_crystal_F_000             548
_exptl_crystal_recrystallization_method EtOH/MeOH
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 645 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         1911
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0281
_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^)+(0.0389P)^2^+0.6219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0739
_reflns_Friedel_coverage         0.540
_reflns_Friedel_fraction_full    0.657
_reflns_Friedel_fraction_max     0.613
_reflns_number_gt                1875
_reflns_number_total             1911
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01596c2.cif
_cod_data_source_block           syl-06-23_2
_cod_depositor_comments
'Adding full bibliography for 7159603--7159605.cif.'
_cod_original_cell_volume        1211.31(4)
_cod_original_formula_sum        'C12 H15 Cl N3 O1.50'
_cod_database_code               7159604
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C13 H14 N4 O2'
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.447
_reflns_odcompleteness_completeness 99.92
_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, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O2-H2C
 0.85 with sigma of 0.02
3.a Free rotating group:
 O2(H2C)
3.b Ternary CH refined with riding coordinates:
 C9(H9)
3.c Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C8(H8A,H8B), C11(H11A,H11B)
3.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
3.e X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_shelx_res_checksum              98080
_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 1.872
_oxdiff_exptl_absorpt_empirical_full_min 0.499