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_7130924
_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         'C31 H28 N4 O4'
_chemical_formula_sum            'C31 H28 N4 O4'
_chemical_formula_weight         520.57
_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                 102.270(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8770(3)
_cell_length_b                   40.4437(13)
_cell_length_c                   8.8989(3)
_cell_measurement_reflns_used    7557
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.0100
_cell_measurement_theta_min      3.3190
_cell_volume                     2770.21(17)
_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                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.937
_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    -62.00 -35.78   0.38   15.00    --   -9.95 136.00 114.00   69
  2  \w    -63.00  -8.66   0.38   15.00    --   -9.95 133.00 -63.00  143
  3  \w     10.00  36.22   0.38   15.00    --   10.22-133.00-131.00   69
  4  \w     13.00  38.08   0.38   15.00    --   10.22-136.00  50.00   66
  5  \w     17.00  43.22   0.38   15.00    --   -9.95  57.00 -30.00   69
  6  \w    -52.00 -24.64   0.38   15.00    --   -9.95 125.00-180.00   72
  7  \w    -53.00 -25.64   0.38   15.00    --   -9.95 -38.00  30.00   72
  8  \w     10.00  36.22   0.38   15.00    --   10.22-125.00 -30.00   69
  9  \w    -17.00  17.20   0.38   15.00    --   10.22 -99.00-180.00   90
 10  \w    -19.00  33.06   0.38   15.00    --   10.22 -99.00 -30.00  137
 11  \w    -53.00 -15.76   0.38   15.00    --   10.22 -57.00  60.00   98
 12  \w      8.00  58.16   0.38   15.00    --   10.22-125.00  90.00  132
 13  \w     -1.00  72.72   0.38   15.00    --   10.22  38.00 -60.00  194
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0401680000
_diffrn_orient_matrix_UB_12      -0.0034401000
_diffrn_orient_matrix_UB_13      -0.0624485000
_diffrn_orient_matrix_UB_21      -0.0037974000
_diffrn_orient_matrix_UB_22      -0.0171757000
_diffrn_orient_matrix_UB_23      0.0151288000
_diffrn_orient_matrix_UB_31      -0.0828475000
_diffrn_orient_matrix_UB_32      -0.0008818000
_diffrn_orient_matrix_UB_33      -0.0502418000
_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  0.0606
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23801
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.090
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78219
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       needle
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.025
_exptl_crystal_size_mid          0.022
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         5313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0688
_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^)+(0.1030P)^2^+0.1365P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1770
_refine_ls_wR_factor_ref         0.2144
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2807
_reflns_number_total             5313
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04870a2.cif
_cod_data_source_block           iiserm-2nd
_cod_original_cell_volume        2770.19(18)
_cod_database_code               7130924
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O S'
_reflns_odcompleteness_completeness 93.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{N3B, N3A}
{C19A, C19B}
3. Uiso/Uaniso restraints and constraints
Uanis(N3B) = Uanis(N3A)
Uanis(O2A) = Uanis(O2B)
Uanis(C19A) = Uanis(C19B)
4. Others
 Sof(O2B)=Sof(N3A)=Sof(H3A)=Sof(C19A)=1-FVAR(1)
 Sof(N3B)=Sof(H3B)=Sof(C19B)=Sof(O2A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C12(H12), C11(H11)
5.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B)
5.c Aromatic/amide H refined with riding coordinates:
 N3B(H3B), N1(H1), C14(H14), C18(H18), C16(H16), C17(H17), C7(H7), C29(H29),
 C5(H5), C3(H3), C8(H8), C9(H9), C4(H4), C26(H26), C28(H28), C27(H27), N3A(H3A)
5.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              97002
_shelx_hkl_checksum              87396
_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 1.501
_oxdiff_exptl_absorpt_empirical_full_min 0.850