Chemoselective Minisci alkylation in aqueous medium: a general strategy for functionalization of complex N-heteroarenes and biomolecules
Hu, Qi-Long; Deng, Jun-Jie; Ye, Jia; Li, Jian; Chan, Albert S. C.; Su, Hang; Xiong, Xiao-Feng; Green Chemistry 27 (2025) 13944–13952; doi:10.1039/D5GC04621A

data_7251024
_publ_section_title
;
 Chemoselective Minisci alkylation in aqueous medium: a general strategy
 for functionalization of complex N-heteroarenes and biomolecules
;
_journal_issue                   43
_journal_name_full               'Green Chemistry'
_journal_page_first              13944
_journal_page_last               13952
_journal_paper_doi               10.1039/D5GC04621A
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C11 H12 N2 O'
_chemical_formula_sum            'C11 H12 N2 O'
_chemical_formula_weight         188.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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             2024-01-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-03-13 deposited with the CCDC.	2025-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                76.951(3)
_cell_angle_beta                 82.321(3)
_cell_angle_gamma                80.632(3)
_cell_formula_units_Z            2
_cell_length_a                   4.8344(2)
_cell_length_b                   8.9159(3)
_cell_length_c                   11.6752(4)
_cell_measurement_reflns_used    2681
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3630
_cell_measurement_theta_min      3.8910
_cell_volume                     481.24(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.941
_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     44.00  70.00   0.50    0.05    --  105.85-125.00 150.00   52
  2  \w     73.00 111.00   0.50    0.05    --  105.85-125.00 150.00   76
  3  \w     64.00 109.00   0.50    0.05    --  105.85-125.00  30.00   90
  4  \w     65.00 106.00   0.50    0.05    --  105.85 -94.00  30.00   82
  5  \w     11.00  41.00   0.50    0.05    --   44.84-112.00-162.00   60
  6  \w     44.00  70.00   0.50    0.05    --   44.84-112.00-162.00   52
  7  \w     70.00 106.00   0.50    0.05    --  105.85-112.00-162.00   72
  8  \w    -30.00  22.00   0.50    0.05    --   44.84 -38.00   0.00  104
  9  \w     38.00 106.00   0.50    0.05    --  105.85 -77.00 120.00  136
 10  \w     43.00  69.00   0.50    0.05    --  105.85 -61.00  60.00   52
 11  \w     33.00  71.00   0.50    0.05    --  105.85 -61.00  30.00   76
 12  \w     37.00  65.00   0.50    0.05    --  105.85 -61.00 -60.00   56
 13  \w     36.00  73.00   0.50    0.05    --  105.85 -61.00 -90.00   74
 14  \w     48.00  73.00   0.50    0.05    --  105.85 -61.00-120.00   50
 15  \w     41.00  73.00   0.50    0.05    --  105.85 -61.00-150.00   64
 16  \w     90.00 116.00   0.50    0.05    --  105.85 112.00 -69.00   52
 17  \w    126.00 173.00   0.50    0.05    --  105.85  15.00 -90.00   94
 18  \w     80.00 106.00   0.50    0.05    --  105.85  15.00 -90.00   52
 19  \w     91.00 177.00   0.50    0.05    --  105.85  30.00  30.00  172
 20  \w     82.00 109.00   0.50    0.05    --   44.84  38.00 120.00   54
 21  \w     32.00  69.00   0.50    0.05    --   44.84  38.00 120.00   74
 22  \w    -24.00  28.00   0.50    0.05    --  -44.84  19.00  90.00  104
 23  \w    -58.00 -28.00   0.50    0.05    -- -100.00  61.00  60.00   60
 24  \w    -55.00 -27.00   0.50    0.05    -- -100.00  61.00  30.00   56
 25  \w    -24.00  32.00   0.50    0.05    --  -44.84  19.00 -30.00  112
 26  \w    -22.00  32.00   0.50    0.05    --  -44.84  19.00-150.00  108
 27  \w    -57.00 -27.00   0.50    0.05    -- -100.00  61.00-120.00   60
 28  \w    -82.00 -57.00   0.50    0.05    -- -100.00  77.00-120.00   50
 29  \w    -42.00 -15.00   0.50    0.05    --  -44.84 112.00 -69.00   54
 30  \w   -100.00 -70.00   0.50    0.05    -- -100.00 112.00 -69.00   60
 31  \w   -164.00 -82.00   0.50    0.05    -- -100.00 -30.00 150.00  164
 32  \w   -169.00-141.00   0.50    0.05    -- -100.00 -45.00 -90.00   56
 33  \w   -128.00 -90.00   0.50    0.05    -- -100.00 -45.00 -90.00   76
 34  \w   -170.00-136.00   0.50    0.05    -- -100.00-125.00-120.00   68
 35  \w   -128.00 -84.00   0.50    0.05    -- -100.00-112.00-162.00   88
 36  \w   -116.00 -84.00   0.50    0.05    -- -100.00-125.00-120.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0355404000
_diffrn_orient_matrix_UB_12      0.1744357000
_diffrn_orient_matrix_UB_13      -0.0577480000
_diffrn_orient_matrix_UB_21      0.1186223000
_diffrn_orient_matrix_UB_22      -0.0393055000
_diffrn_orient_matrix_UB_23      -0.1205245000
_diffrn_orient_matrix_UB_31      -0.3000803000
_diffrn_orient_matrix_UB_32      -0.0095907000
_diffrn_orient_matrix_UB_33      -0.0259602000
_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  0.0228
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4360
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.531
_diffrn_reflns_theta_min         3.906
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
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    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0715P)^2^+0.0617P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1197
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1646
_reflns_number_total             1880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc04621a2.cif
_cod_data_source_block           huql_tm_240125_auto
_cod_depositor_comments
'Adding full bibliography for 7251023--7251025.cif.'
_cod_database_code               7251024
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     'C H N F'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C8(H8), C7(H7)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              6967
_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 1.671
_oxdiff_exptl_absorpt_empirical_full_min 0.718