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_7159603
_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         'C13 H13 N3 O'
_chemical_formula_sum            'C13 H13 N3 O'
_chemical_formula_weight         227.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.45921(12)
_cell_length_b                   15.7500(3)
_cell_length_c                   21.1734(4)
_cell_measurement_reflns_used    7010
_cell_measurement_temperature    113(1)
_cell_measurement_theta_max      71.9270
_cell_measurement_theta_min      3.5110
_cell_volume                     2154.02(7)
_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      113(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 0.943
_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    -43.00  25.00   0.50    0.75    --  -47.23  38.00   0.00  136
  2  \w    -37.00 -12.00   0.50    3.00    --  -90.25  45.00 -30.00   50
  3  \w    -45.00 -12.00   0.50    3.00    --  -90.25  45.00 -60.00   66
  4  \w    -63.00 -22.00   0.50    0.75    --  -47.23  65.00   3.00   82
  5  \w    -37.00 -11.00   0.50    3.00    --  -90.25 111.00 -90.00   52
  6  \w    -61.00 -29.00   0.50    3.00    --  -90.25  65.00   3.00   64
  7  \w    -83.00 -54.00   0.50    3.00    --  -90.25 111.00 -90.00   58
  8  \w    -50.00 -19.00   0.50    3.00    --  -90.25  45.00-150.00   62
  9  \w    -95.00 -69.00   0.50    3.00    --  -90.25 -45.00 -30.00   52
 10  \w   -114.00 -75.00   0.50    0.75    --  -47.23-125.00 -60.00   78
 11  \w   -108.00 -78.00   0.50    0.75    --  -47.23-125.00 -90.00   60
 12  \w   -156.00-101.00   0.50    3.00    --  -90.25 -59.00  19.00  110
 13  \w   -116.00 -84.00   0.50    3.00    --  -90.25-108.00 145.00   64
 14  \w   -164.00-114.00   0.50    3.00    --  -90.25 -45.00 -30.00  100
 15  \w    -68.00 -16.00   0.50    3.00    --  -90.25  59.00 159.00  104
 16  \w     25.00  50.00   0.50    3.00    --   97.33 -65.00-131.00   50
 17  \w     22.00  47.00   0.50    3.00    --   97.33 -45.00 -90.00   50
 18  \w     20.00  45.00   0.50    3.00    --   97.33 -45.00-120.00   50
 19  \w     21.00  46.00   0.50    3.00    --   97.33 -45.00  60.00   50
;
_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      0.2249889000
_diffrn_orient_matrix_UB_12      -0.0006245000
_diffrn_orient_matrix_UB_13      0.0240781000
_diffrn_orient_matrix_UB_21      0.0554462000
_diffrn_orient_matrix_UB_22      -0.0686088000
_diffrn_orient_matrix_UB_23      -0.0489849000
_diffrn_orient_matrix_UB_31      0.0564335000
_diffrn_orient_matrix_UB_32      0.0697226000
_diffrn_orient_matrix_UB_33      -0.0481087000
_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  0.0388
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9625
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.521
_diffrn_reflns_theta_min         3.497
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38199
_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_density_diffrn    1.402
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1345 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0558P)^2^+0.0967P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0926
_reflns_Friedel_coverage         0.644
_reflns_Friedel_fraction_full    0.902
_reflns_Friedel_fraction_max     0.829
_reflns_number_gt                3575
_reflns_number_total             3813
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01596c2.cif
_cod_data_source_block           syl-06-08
_cod_depositor_comments
;
Adding full bibliography for 7159603--7159605.cif.

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C26 H26 N6 O2'
_cod_original_formula_weight         454.53
_cod_original_formula_moiety         '2(C13 H13 N3 O)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        2154.03(7)
_cod_database_code               7159603
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C13 H16 N4 O'
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.781
_reflns_odcompleteness_completeness 99.91
_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
2.a Ternary CH refined with riding coordinates:
 C12(H12), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B), C22(H22A,H22B), C23(H23A,H23B),
 C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), N4(H4A), N6(H6), C15(H15),
 C16(H16), C17(H17), C18(H18)
;
_shelx_res_checksum              84065
_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 1.955
_oxdiff_exptl_absorpt_empirical_full_min 0.540