Azobenzene-based unnatural amino acid scaffolds via Pd(II)-catalyzed C(sp3)-H arylation strategy
Tomar, Radha; Suwasia, Sonam; Roychoudhury, Angshuman; Venkataramani, Sugumar; Babu, Srinivasarao Arulananda; Chemical Communications  (2022) –; doi:10.1039/D2CC04870A

data_7130925
_publ_section_title
;
 Azobenzene-based unnatural amino acid scaffolds via Pd(II)-catalyzed
 C(sp3)-H arylation strategy
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04870A
_journal_year                    2022
_chemical_formula_moiety         'C32 H27 N3 O4 S'
_chemical_formula_sum            'C32 H27 N3 O4 S'
_chemical_formula_weight         549.62
_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
_audit_creation_date             2022-10-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-10-25 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.069(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.4643(6)
_cell_length_b                   8.6783(2)
_cell_length_c                   15.5406(5)
_cell_measurement_reflns_used    12929
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.1710
_cell_measurement_theta_min      3.3230
_cell_volume                     2759.46(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -78.00 -53.00   0.50   15.00    --   -9.79 166.00-178.00   50
  2  \w    -52.00 -27.00   0.50   15.00    --   -9.79 116.00  34.00   50
  3  \w     38.00  64.00   0.50   15.00    --   10.07-166.00 159.00   52
  4  \w     26.00  53.00   0.50   15.00    --   10.07-116.00 -53.00   54
  5  \w    -54.00 -22.00   0.50   15.00    --   -9.79 125.00 120.00   64
  6  \w    -73.00   4.00   0.50   15.00    --   -9.79 -38.00-150.00  154
  7  \w    -30.00  -5.00   0.50   15.00    --   -9.79 125.00 -60.00   50
  8  \w    -22.00  35.00   0.50   15.00    --   -9.79  19.00  30.00  114
  9  \w    -72.00 -46.00   0.50   15.00    --   -9.79 -57.00 -60.00   52
 10  \w    -33.00  -7.00   0.50   15.00    --   10.07 131.00-179.16   52
 11  \w    -34.00   0.00   0.50   15.00    --   10.07 119.00  12.93   68
 12  \w     26.00  58.00   0.50   15.00    --   10.07-125.00  60.00   64
 13  \w     25.00  67.00   0.50   15.00    --   10.07  19.00  90.00   84
 14  \w    -17.00  41.00   0.50   15.00    --   10.07 -99.00-120.00  116
 15  \w    -12.00  43.00   0.50   15.00    --   10.07 -99.00 150.00  110
 16  \w     -4.00  35.00   0.50   15.00    --   10.07 -99.00   0.00   78
 17  \w    -60.00  22.00   0.50   15.00    --   10.07 -19.00  60.00  164
 18  \w     -2.00  67.00   0.50   15.00    --   10.07  19.00-120.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            37375
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.263
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.018
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0592P)^2^+0.2001P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1368
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3418
_reflns_number_total             5639
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04870a2.cif
_cod_data_source_block           iiserm-rt869
_cod_original_cell_volume        2759.45(14)
_cod_database_code               7130925
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C13(H13), C12(H12), C27(H27), C15(H15), C16(H16), C28(H28),
 C24(H24), C20(H20), C2(H2A), C30(H30), C29(H29), C21(H21), C22(H22), C23(H23),
 C3(H3), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              86515
_shelx_hkl_checksum              34052
_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
;