Diastereoselective palladium-catalyzed C(sp3)–H cyanomethylation of amino acid and carboxylic acid derivatives
Garai, Sumit; Ghosh, Krishna Gopal; Biswas, Ashik; Chowdhury, Sushobhan; Sureshkumar, Devarajulu; Chemical Communications  (2022) –; doi:10.1039/D2CC03106J

data_7130277
_publ_section_title
;
 Diastereoselective palladium-catalyzed C(sp3)--H cyanomethylation of
 amino acid and carboxylic acid derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03106J
_journal_year                    2022
_chemical_formula_moiety         'C18 H16 N4 O'
_chemical_formula_sum            'C18 H16 N4 O'
_chemical_formula_weight         304.35
_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             2021-12-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-21 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.911(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4867(3)
_cell_length_b                   12.6562(5)
_cell_length_c                   14.6198(6)
_cell_measurement_reflns_used    5143
_cell_measurement_temperature    295.9(6)
_cell_measurement_theta_max      27.2240
_cell_measurement_theta_min      2.1220
_cell_volume                     1551.35(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.921
_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    -11.00 103.00   1.00   22.00    --   26.72  57.00  90.00  114
  2  \w    -29.00 108.00   1.00   22.00    --   26.72  38.00-120.00  137
  3  \w    -11.00 103.00   1.00   22.00    --   26.72  57.00 -30.00  114
  4  \w     35.00 121.00   1.00   22.00    --   26.72 178.00  90.00   86
  5  \w    -49.00  31.00   1.00   22.00    --   26.72 -57.00-150.00   80
  6  \w     35.00 121.00   1.00   22.00    --   26.72 178.00 -90.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0280756000
_diffrn_orient_matrix_UB_12      -0.0461077000
_diffrn_orient_matrix_UB_13      0.0198137000
_diffrn_orient_matrix_UB_21      -0.0657353000
_diffrn_orient_matrix_UB_22      -0.0021250000
_diffrn_orient_matrix_UB_23      -0.0364514000
_diffrn_orient_matrix_UB_31      0.0453174000
_diffrn_orient_matrix_UB_32      -0.0317095000
_diffrn_orient_matrix_UB_33      -0.0263203000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13574
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.649
_diffrn_reflns_theta_min         2.140
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0535
_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^)+(0.0468P)^2^+0.5846P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1517
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2647
_reflns_number_total             3335
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03106j2.cif
_cod_data_source_block           test_1
_cod_database_code               7130277
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H16 N4 O'
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.997
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C004(H004), C008(H008), C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B), C00H(H00D,H00E), C00K(H00F,H00G)
2.c Aromatic/amide H refined with riding coordinates:
 N002(H002), C00C(H00C), C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M),
 C00N(H00N)
;
_shelx_res_checksum              1351
_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 1.761
_oxdiff_exptl_absorpt_empirical_full_min 0.640