Enantiopure and quasiracemic crystals of 7-substituted tryptophan derivatives: modulation of the molecular arrangement for functionalized crystals
Tsuchiya, Yuiho; Ohata, Misaki; Chisuga, Taichi; Nakano, Shogo; Ito, Suguru; CrystEngComm 27 (2025) 3095–3101; doi:10.1039/D5CE00099H

data_7250212
_publ_section_title
;
 Enantiopure and quasiracemic crystals of 7-substituted tryptophan
 derivatives: modulation of the molecular arrangement for functionalized
 crystals
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              3095
_journal_page_last               3101
_journal_paper_doi               10.1039/D5CE00099H
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C10 H11 N3 O2'
_chemical_formula_sum            'C10 H11 N3 O2'
_chemical_formula_weight         205.22
_space_group_crystal_system      tetragonal
_space_group_IT_number           79
_space_group_name_Hall           'I 4'
_space_group_name_H-M_alt        'I 4'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-18
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-23 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.69560(8)
_cell_length_b                   18.69560(8)
_cell_length_c                   5.95062(4)
_cell_measurement_reflns_used    5593
_cell_measurement_temperature    223
_cell_measurement_theta_max      71.18
_cell_measurement_theta_min      4.73
_cell_volume                     2079.893(19)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      223
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6721
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.652
_diffrn_reflns_theta_min         4.731
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.66a (Rigaku Oxford Diffraction, 2019)

Empirical absorption correction using spherical harmonics,

 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: THF/H2O'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 838 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1974
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+0.3361P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0619
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                1942
_reflns_number_total             1974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00099h2.cif
_cod_data_source_block           tyh237_entry11_dry
_cod_depositor_comments
'Adding full bibliography for 7250211--7250214.cif.'
_cod_original_cell_volume        2079.89(2)
_cod_database_code               7250212
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.651
_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,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C4(H4), C6(H6), C5(H5)
2.d Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              65518
_shelx_fab_checksum              37003
_olex2_submission_special_instructions 'No special instructions were received'