Multifunctional 3-cyanopyridine compounds: synthesis based on a tandem reaction with 100% atom economy and their applications
Cao, Xi-Ying; Li, Zhong-Hao; Cao, Xiao-Hui; Li, Zong; Pang, Chu-Ming; Zhang, Zu-Qi; Wang, Zhao-Yang; Green Chemistry 27 (2025) 7300–7306; doi:10.1039/D5GC01264C

data_7250418
_publ_section_title
;
 Multifunctional 3-cyanopyridine compounds: synthesis based on a tandem
 reaction with 100% atom economy and their applications
;
_journal_issue                   24
_journal_name_full               'Green Chemistry'
_journal_page_first              7300
_journal_page_last               7306
_journal_paper_doi               10.1039/D5GC01264C
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 Cl N3 O'
_chemical_formula_sum            'C17 H16 Cl N3 O'
_chemical_formula_weight         313.78
_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             2024-07-21
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-28 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.609(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1028(13)
_cell_length_b                   8.8291(16)
_cell_length_c                   12.7916(17)
_cell_measurement_reflns_used    1704
_cell_measurement_temperature    297
_cell_measurement_theta_max      22.1420
_cell_measurement_theta_min      3.1900
_cell_volume                     798.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.849
_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     -9.00  82.00   1.00    1.50    --   17.12  72.00 176.00   91
  2  \w    -51.00  43.00   1.00    1.50    --   17.12 -72.00  46.00   94
  3  \w    -89.00  -4.00   1.00    1.50    --  -17.59 -19.00-120.00   85
  4  \w    -28.00  -1.00   1.00    1.50    --  -17.59  77.00 -90.00   27
  5  \w    -38.00   1.00   1.00    1.50    --  -17.59 -77.00 -60.00   39
  6  \w    -36.00  -2.00   1.00    1.50    --  -17.59 -77.00-150.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0892524000
_diffrn_orient_matrix_UB_12      0.0200790000
_diffrn_orient_matrix_UB_13      -0.0166280000
_diffrn_orient_matrix_UB_21      0.0461163000
_diffrn_orient_matrix_UB_22      -0.0446383000
_diffrn_orient_matrix_UB_23      0.0408670000
_diffrn_orient_matrix_UB_31      -0.0043813000
_diffrn_orient_matrix_UB_32      -0.0635992000
_diffrn_orient_matrix_UB_33      -0.0339295000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6298
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.314
_diffrn_reflns_theta_min         2.808
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.99a (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    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 874 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3542
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0459P)^2^+0.0745P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1159
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.771
_reflns_number_gt                2648
_reflns_number_total             3542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc01264c2.cif
_cod_data_source_block           exp_14531_auto
_cod_depositor_comments
'Adding full bibliography for 7250417--7250418.cif.'
_cod_database_code               7250418
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
N3 \\sim C13 \\sim C13A \\sim C14 \\sim C14A \\sim C15 \\sim C15A \\sim C16:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
3. Others
 Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C15A)=
 Sof(H15C)=Sof(H15D)=Sof(H16C)=Sof(H16D)=1-FVAR(1)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=
 Sof(H15B)=Sof(H16A)=Sof(H16B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C13A(H13C,H13D), C14(H14A,H14B), C14A(H14C,H14D), C15(H15A,
 H15B), C15A(H15C,H15D), C16(H16A,H16B), C16(H16C,H16D)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8)
4.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              4425
_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 1.292
_oxdiff_exptl_absorpt_empirical_full_min 0.628