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_7250211
_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_formula_moiety         'C12 H11 N3 O2'
_chemical_formula_sum            'C12 H11 N3 O2'
_chemical_formula_weight         229.24
_chemical_name_common            7_Cyano_L_Trp
_chemical_name_systematic        7_Cyano_L_Trp
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-23
_audit_creation_method
;
Olex2 1.5-ac7-002
(compiled 2024.05.10 svn.r6303ca7c for Rigaku Oxford Diffraction, GUI svn.r6967)
;
_audit_update_record
;
2025-01-22 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.86(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.81(12)
_cell_length_b                   4.94(8)
_cell_length_c                   17.74(13)
_cell_measurement_reflns_used    1605
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      0.9240
_cell_measurement_theta_min      0.0700
_cell_volume                     1030(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.105a 64-bit (release 11-01-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac7-002 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-002 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix-ED
_diffrn_measured_fraction_theta_full 0.649
_diffrn_measured_fraction_theta_max 0.647
_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    -60.00  60.00   0.15    0.15    --    0.00   0.00   0.00  800
;
_diffrn_measurement_device       'electron diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy-ED, HyPix-ED, electron source at 200keV'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0014559000
_diffrn_orient_matrix_UB_12      -0.0000496000
_diffrn_orient_matrix_UB_13      -0.0011348000
_diffrn_orient_matrix_UB_21      0.0001789000
_diffrn_orient_matrix_UB_22      -0.0050490000
_diffrn_orient_matrix_UB_23      -0.0000802000
_diffrn_orient_matrix_UB_31      -0.0015536000
_diffrn_orient_matrix_UB_32      -0.0005580000
_diffrn_orient_matrix_UB_33      0.0008541000
_diffrn_radiation_monochromator  'transmission electron microscope'
_diffrn_radiation_probe          electron
_diffrn_radiation_type           'transmission electron microscope'
_diffrn_radiation_wavelength     0.0251
_diffrn_reflns_av_R_equivalents  0.1247
_diffrn_reflns_av_unetI/netI     0.2236
_diffrn_reflns_Laue_measured_fraction_full 0.649
_diffrn_reflns_Laue_measured_fraction_max 0.647
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6125
_diffrn_reflns_point_group_measured_fraction_full 0.702
_diffrn_reflns_point_group_measured_fraction_max 0.692
_diffrn_reflns_theta_full        0.863
_diffrn_reflns_theta_max         0.946
_diffrn_reflns_theta_min         0.070
_diffrn_source                   'transmission electron microscope'
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       needle
_exptl_crystal_F_000             186
_exptl_crystal_size_max          0.001
_exptl_crystal_size_mid          0.001
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_extinction_coef       9405(20)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3407
_refine_ls_number_restraints     259
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.2544
_refine_ls_R_factor_gt           0.1854
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4603
_refine_ls_wR_factor_ref         0.5176
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.770
_reflns_Friedel_fraction_max     0.750
_reflns_number_gt                1245
_reflns_number_total             3407
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00099h2.cif
_cod_data_source_block           1108_1
_cod_depositor_comments
'Adding full bibliography for 7250211--7250214.cif.'
_cod_original_cell_volume        1030(21)
_cod_database_code               7250211
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_scatteringfactors_ed
;
Peng,L.M. (1999) Micron 30, 625-648
;
_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. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C016(H016), C020(H020)
3.b Secondary CH2 refined with riding coordinates:
 C019(H01A,H01B), C030(H03A,H03B)
3.c Aromatic/amide H refined with riding coordinates:
 N007(H007), C011(H011), C014(H014), C015(H015), C021(H021), N022(H022),
 C026(H026), C025(H025), C027(H027), C028(H028)
3.d Fitted pentagon refined as free rotating group:
 C023(N022,C026,C032,C018)
3.e Idealised Me refined as rotating group:
 N009(H00A,H00B,H00C), N012(H01C,H01D,H01E)
;
_shelx_res_checksum              78991
_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 2.149
_oxdiff_exptl_absorpt_empirical_full_min 0.546