Synthesis of 3-arylamino-2-polyhydroxyalkyl-substituted indoles from unprotected saccharides and anilines
Wu, Jilai; Zhou, Likai; Xie, Song; Wei, Chao; Li, Xiaoliu; Chen, Hua; Green Chemistry 26 (2024) 1883–1888; doi:10.1039/D3GC04440H

data_7248078
_publ_section_title
;
 Synthesis of 3-arylamino-2-polyhydroxyalkyl-substituted indoles from
 unprotected saccharides and anilines
;
_journal_issue                   4
_journal_name_full               'Green Chemistry'
_journal_page_first              1883
_journal_page_last               1888
_journal_paper_doi               10.1039/D3GC04440H
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C18 H20 N2 O2'
_chemical_formula_sum            'C18 H20 N2 O2'
_chemical_formula_weight         296.36
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-10-17 deposited with the CCDC.	2024-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                75.371(3)
_cell_angle_beta                 87.564(2)
_cell_angle_gamma                85.468(3)
_cell_formula_units_Z            2
_cell_length_a                   5.4476(4)
_cell_length_b                   9.3390(8)
_cell_length_c                   15.3977(12)
_cell_measurement_reflns_used    2190
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.853
_cell_measurement_theta_min      2.260
_cell_volume                     755.39(10)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0976
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8184
_diffrn_reflns_point_group_measured_fraction_full 0.807
_diffrn_reflns_point_group_measured_fraction_max 0.785
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.422
_diffrn_reflns_theta_min         2.259
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1228 before and 0.0691 after correction.
The Ratio of minimum to maximum transmission is 0.7167.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1185 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         4859
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0416P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1295
_reflns_Friedel_coverage         0.608
_reflns_Friedel_fraction_full    0.630
_reflns_Friedel_fraction_max     0.594
_reflns_number_gt                3848
_reflns_number_total             4859
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc04440h2.cif
_cod_data_source_block           450_0m
_cod_depositor_comments
'Adding full bibliography for 7248078--7248079.cif.'
_cod_database_code               7248078
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N3-H3B = O3-H3A
 0.87 with sigma of 0.02
 N2-H2A
 0.87 with sigma of 0.02
 O4-H4A
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C11(H11), C10(H10), C21(H21), C20(H20)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C22(H22A,H22B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), N4(H4B), C5(H5), C15(H15), C18(H18), C14(H14), C26(H26), C33(H33),
 C32(H32), C17(H17), C2(H2B), C3(H3), C28(H28), C35(H35), C34(H34), C36(H36),
 C16(H16), C4(H4), C27(H27), C30(H30)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'