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_7250417
_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_formula_moiety         'C18 H19 N3 O'
_chemical_formula_sum            'C18 H19 N3 O'
_chemical_formula_weight         293.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 110.066(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8541(7)
_cell_length_b                   8.4683(5)
_cell_length_c                   15.3887(9)
_cell_measurement_reflns_used    3755
_cell_measurement_temperature    200
_cell_measurement_theta_max      28.3170
_cell_measurement_theta_min      3.0010
_cell_volume                     1573.41(17)
_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      200
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.887
_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      4.00  86.00   1.00    1.50    --   17.28  57.00-180.00   82
  2  \w      2.00  62.00   1.00    1.50    --   17.28  57.00   0.00   60
  3  \w    -51.00  20.00   1.00    1.50    --   17.28 -57.00  30.00   71
  4  \w      3.00  86.00   1.00    1.50    --   17.28  57.00 -90.00   83
  5  \w    -39.00  26.00   1.00    1.50    --   17.28 -77.00 120.00   65
  6  \w    -26.00  17.00   1.00    1.50    --  -17.59 -92.00  61.00   43
;
_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      0.0111226000
_diffrn_orient_matrix_UB_12      -0.0755015000
_diffrn_orient_matrix_UB_13      0.0211566000
_diffrn_orient_matrix_UB_21      0.0093533000
_diffrn_orient_matrix_UB_22      -0.0304226000
_diffrn_orient_matrix_UB_23      -0.0396111000
_diffrn_orient_matrix_UB_31      0.0569276000
_diffrn_orient_matrix_UB_32      0.0198079000
_diffrn_orient_matrix_UB_33      0.0197398000
_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  0.0279
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13077
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.274
_diffrn_reflns_theta_min         2.743
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95005
_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    1.238
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0645
_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^)+(0.0786P)^2^+0.7730P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1742
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2847
_reflns_number_total             3816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc01264c2.cif
_cod_data_source_block           exp_14529_auto
_cod_depositor_comments
'Adding full bibliography for 7250417--7250418.cif.'
_cod_database_code               7250417
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C8(H8)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              37916
_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 1.165
_oxdiff_exptl_absorpt_empirical_full_min 0.892