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_7130278
_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         'C28 H20 N4 O3'
_chemical_formula_sum            'C28 H20 N4 O3'
_chemical_formula_weight         460.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-16
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-02-16 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.74610(10)
_cell_length_b                   15.1159(3)
_cell_length_c                   22.0277(3)
_cell_measurement_reflns_used    7340
_cell_measurement_temperature    100.00(13)
_cell_measurement_theta_max      67.9760
_cell_measurement_theta_min      3.4780
_cell_volume                     2246.24(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_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    -37.00  28.00   0.50    1.50    --  -40.33  32.00 -39.00  130
  2  \w    -44.00 -15.00   0.50    4.00    --  -82.50  42.00-120.00   58
  3  \w    -56.00 -30.00   0.50    4.00    --  -82.50 125.00-179.00   52
  4  \w    -87.00 -12.00   0.50    1.50    --  -40.33 125.00-179.00  150
  5  \w     67.00  93.00   0.50    1.50    --   40.33  32.00 -39.00   52
  6  \w     84.00 137.00   0.50    4.00    --   96.67  32.00 -39.00  106
  7  \w    106.00 170.00   0.50    4.00    --   96.67  96.00-150.00  128
  8  \w     97.00 161.00   0.50    4.00    --   96.67 125.00-179.00  128
  9  \w     30.00  56.00   0.50    4.00    --   96.67 -50.00-180.00   52
 10  \w     30.00  56.00   0.50    4.00    --   96.67 -50.00-120.00   52
 11  \w     30.00  55.00   0.50    4.00    --   96.67 -50.00 -90.00   50
 12  \w     33.00  62.00   0.50    4.00    --   96.67 -59.00 -60.00   58
 13  \w     46.00 107.00   0.50    4.00    --   96.67 -91.00  -7.00  122
 14  \w     62.00  87.00   0.50    4.00    --   96.67-147.00 -63.00   50
 15  \w     60.00  94.00   0.50    1.50    --   40.33-147.00 -63.00   68
 16  \w     31.00  56.00   0.50    4.00    --   96.67 -50.00  60.00   50
 17  \w     51.00  81.00   0.50    4.00    --   96.67 -68.00 120.00   60
 18  \w     40.00  68.00   0.50    4.00    --   96.67 -59.00 150.00   56
 19  \w     31.00  57.00   0.50    4.00    --   96.67 -50.00 120.00   52
 20  \w     39.00  64.00   0.50    1.50    --   40.33-125.00 102.00   50
 21  \w      5.00  31.00   0.50    1.50    --   40.33 -32.00 161.00   52
 22  \w    124.00 150.00   0.50    4.00    --   96.67  91.00 105.00   52
 23  \w     23.00 104.00   0.50    1.50    --   40.33  50.00-180.00  162
 24  \w    -70.00 -45.00   0.50    4.00    --  -82.50  91.00 105.00   50
 25  \w    -72.00  31.00   0.50    1.50    --  -40.33  91.00 105.00  206
 26  \w    -74.00 -27.00   0.50    1.50    --  -40.33 -32.00 161.00   94
 27  \w   -118.00 -92.00   0.50    4.00    --  -82.50 -32.00 161.00   52
 28  \w   -134.00-109.00   0.50    4.00    --  -82.50 -91.00  -7.00   50
 29  \w   -128.00-103.00   0.50    4.00    --  -82.50-147.00 -63.00   50
 30  \w   -102.00 -24.00   0.50    1.50    --  -40.33 147.00 -13.00  156
 31  \w    -87.00 -62.00   0.50    4.00    --  -82.50 147.00 -13.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1367020000
_diffrn_orient_matrix_UB_12      -0.0790940000
_diffrn_orient_matrix_UB_13      -0.0139040000
_diffrn_orient_matrix_UB_21      -0.1585422000
_diffrn_orient_matrix_UB_22      0.0638631000
_diffrn_orient_matrix_UB_23      -0.0248399000
_diffrn_orient_matrix_UB_31      0.0914232000
_diffrn_orient_matrix_UB_32      -0.0075766000
_diffrn_orient_matrix_UB_33      -0.0638410000
_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  0.0377
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9827
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.216
_diffrn_reflns_theta_min         3.546
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0328
_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^)+(0.0480P)^2^+0.1014P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0858
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3421
_reflns_number_total             3690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03106j2.cif
_cod_data_source_block           sgmcn
_cod_database_code               7130278
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     100K
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.971
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H006(0.024) H00B(0.023) H00E(0.027) H00G(0.03) H00I(0.031)
 H00J(0.029) H00L(0.03) H00M(0.029) H00O(0.031) H00P(0.031) H00Q(0.034)
 H00R(0.03) H00S(0.025) H00A(0.031) H00C(0.031) H00U(0.03) H00V(0.034)
 H00W(0.034) H00X(0.035) H00Z(0.038)
 Fixed X: H006(-0.393273) H00B(-0.615938) H00E(-0.389704) H00G(-0.40251) H00I(-
 0.407782) H00J(-0.414514) H00L(-0.496891) H00M(-0.744505) H00O(-0.417632)
 H00P(0.120095) H00Q(-0.233593) H00R(-0.179099) H00S(-0.314381) H00A(-0.604923)
 H00C(-0.740842) H00U(-0.395011) H00V(0.068398) H00W(-0.752784) H00X(-0.190565)
 H00Z(-0.472225)
 Fixed Y: H006(-0.636986) H00B(-0.488827) H00E(-0.602871) H00G(-0.864044)
 H00I(-0.882294) H00J(-0.976306) H00L(-0.596405) H00M(-0.366798) H00O(-
 1.002338) H00P(-0.479432) H00Q(-0.58095) H00R(-0.281084) H00S(-0.363728) H00A(-
 0.37332) H00C(-0.348806) H00U(-0.718578) H00V(-0.523079) H00W(-0.306857) H00X(-
 0.219741) H00Z(-0.237233)
 Fixed Z: H006(-0.41868) H00B(-0.398329) H00E(-0.576996) H00G(-0.618674) H00I(-
 0.36144) H00J(-0.532159) H00L(-0.17683) H00M(-0.331139) H00O(-0.428188) H00P(-
 0.24075) H00Q(-0.108052) H00R(-0.350607) H00S(-0.429961) H00A(-0.493754) H00C(-
 0.436475) H00U(-0.64837) H00V(-0.139121) H00W(-0.233089) H00X(-0.252999) H00Z(-
 0.193189)
;
_shelx_res_checksum              29951
_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 1.615
_oxdiff_exptl_absorpt_empirical_full_min 0.696