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_7159605
_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         'C15 H20 N4 O3'
_chemical_formula_sum            'C15 H20 N4 O3'
_chemical_formula_weight         304.35
_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                 112.304(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.2851(13)
_cell_length_b                   5.2346(4)
_cell_length_c                   18.9492(16)
_cell_measurement_reflns_used    1950
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      69.5320
_cell_measurement_theta_min      5.0640
_cell_volume                     1494.5(2)
_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 0.989
_diffrn_measured_fraction_theta_max 0.988
_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    -36.00  14.40   0.80    2.60    --  -46.98  38.00   0.00   63
  2  \w     -8.00  18.40   0.80    2.60    --  -46.98  19.00   0.00   33
  3  \w    -26.00  35.60   0.80    2.60    --  -46.98  19.00  60.00   77
  4  \w    -32.00  29.60   0.80    2.60    --  -46.98  96.00  74.00   77
  5  \w    -45.00 -18.60   0.80   10.60    --  -90.25 111.00   0.00   33
  6  \w    -47.00 -12.60   0.80   10.60    --  -90.25  45.00  30.00   43
  7  \w    -47.00 -11.80   0.80   10.60    --  -90.25  45.00   0.00   44
  8  \w    -50.00 -22.00   0.80   10.60    --  -90.25  45.00 -90.00   35
  9  \w    -49.00 -17.00   0.80   10.60    --  -90.25  45.00-120.00   40
 10  \w    -43.00 -11.80   0.80   10.60    --  -90.25  45.00-150.00   39
 11  \w    -87.00 -24.60   0.80   10.60    --  -90.25  77.00  60.00   78
 12  \w    -79.00 -11.00   0.80   10.60    --  -90.25  96.00  74.00   85
 13  \w     23.00  57.40   0.80    2.60    --   46.98 -96.00 -34.00   43
 14  \w     62.00  86.80   0.80   10.60    --   97.33 -96.00 -34.00   31
 15  \w     61.00  85.80   0.80   10.60    --   97.33 -77.00   0.00   31
 16  \w     40.00  64.80   0.80   10.60    --   97.33 -61.00 -90.00   31
 17  \w     24.00  51.20   0.80   10.60    --   97.33 -77.00   0.00   34
 18  \w     20.00  45.60   0.80   10.60    --   97.33 -45.00 -90.00   32
 19  \w    -29.00  23.00   0.80    2.60    --   46.98 -19.00  30.00   65
 20  \w     26.00  67.60   0.80   10.60    --   97.33 -61.00 120.00   52
 21  \w     32.00  71.20   0.80   10.60    --   97.33 -61.00 150.00   49
 22  \w     20.00  47.20   0.80   10.60    --   97.33 -45.00 120.00   34
 23  \w    140.00 176.00   0.80   10.60    --   97.33 111.00  90.00   45
 24  \w    109.00 143.40   0.80   10.60    --   97.33 178.00 120.00   43
 25  \w     74.00  98.80   0.80   10.60    --   97.33 178.00 120.00   31
 26  \w   -128.00-103.20   0.80   10.60    --  -90.25 -96.00 -34.00   31
 27  \w   -152.00-106.40   0.80   10.60    --  -90.25 -61.00 -30.00   57
;
_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      0.0175935000
_diffrn_orient_matrix_UB_12      0.2575570000
_diffrn_orient_matrix_UB_13      0.0424800000
_diffrn_orient_matrix_UB_21      -0.0922417000
_diffrn_orient_matrix_UB_22      0.0953525000
_diffrn_orient_matrix_UB_23      -0.0532200000
_diffrn_orient_matrix_UB_31      -0.0404494000
_diffrn_orient_matrix_UB_32      -0.1054957000
_diffrn_orient_matrix_UB_33      0.0555774000
_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  0.0507
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4802
_diffrn_reflns_point_group_measured_fraction_full 0.793
_diffrn_reflns_point_group_measured_fraction_max 0.791
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.729
_diffrn_reflns_theta_min         5.874
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73535
_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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       plank
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method MeOH
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 496 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2156
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0874P)^2^+0.0661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1390
_reflns_Friedel_coverage         0.434
_reflns_Friedel_fraction_full    0.544
_reflns_Friedel_fraction_max     0.543
_reflns_number_gt                1870
_reflns_number_total             2156
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01596c2.cif
_cod_data_source_block           syl-06-20_01
_cod_depositor_comments
'Adding full bibliography for 7159603--7159605.cif.'
_cod_database_code               7159605
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H20 N4 O3'
_reflns_odcompleteness_completeness 99.40
_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 C(H,H,H) groups
2. Restrained distances
 N2-H2A = N2-H2B
 0.86 with sigma of 0.02
 H2A-H2B
 1.56 with sigma of 0.02
3.a Riding coordinates:
 N4(H4)
3.b Ternary CH refined with riding coordinates:
 C10(H10)
3.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B)
3.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C3(H3A), C4(H4A), C5(H5), C8(H8)
3.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              68665
_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 2.755
_oxdiff_exptl_absorpt_empirical_full_min 0.645