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_7130923
_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         '2(C28 H27 N3 O4)'
_chemical_formula_sum            'C56 H54 N6 O8'
_chemical_formula_weight         939.05
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                69.902(7)
_cell_angle_beta                 75.360(7)
_cell_angle_gamma                67.226(8)
_cell_formula_units_Z            2
_cell_length_a                   13.6279(11)
_cell_length_b                   14.2193(12)
_cell_length_c                   14.7408(11)
_cell_measurement_reflns_used    11543
_cell_measurement_temperature    160.0(2)
_cell_measurement_theta_max      26.1750
_cell_measurement_theta_min      3.2810
_cell_volume                     2449.6(4)
_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      160.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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    -34.00  -3.00   0.50   10.00    --   -9.79 100.00   8.00   62
  2  \w    -10.00  41.00   0.50   10.00    --   10.07-100.00 -97.00  102
  3  \w    -24.00  14.00   0.50   10.00    --   -9.79 -77.00 -60.00   76
  4  \w    -59.00 -33.00   0.50   10.00    --   -9.79 -77.00 -60.00   52
  5  \w      0.00  53.00   0.50   10.00    --   -9.79  38.00  30.00  106
  6  \w    -60.00  22.00   0.50   10.00    --   10.07 -19.00  30.00  164
  7  \w    -19.00   9.00   0.50   10.00    --   10.07 -99.00 -60.00   56
  8  \w     16.00  43.00   0.50   10.00    --   10.07 -99.00 -60.00   54
  9  \w     -7.00  73.00   0.50   10.00    --   10.07  57.00 120.00  160
 10  \w    -19.00  22.00   0.50   10.00    --   10.07 -99.00   0.00   82
 11  \w    -29.00   1.00   0.50   10.00    --   10.07 121.00-147.03   60
 12  \w    -48.00 -14.00   0.50   10.00    --   10.07 -77.00-180.00   68
 13  \w      8.00  34.00   0.50   10.00    --   10.07 -77.00-180.00   52
 14  \w    -14.00  75.00   0.50   10.00    --   10.07  77.00-180.00  178
 15  \w    -32.00  -6.00   0.50   10.00    --   10.07 132.00 -26.37   52
 16  \w    -53.00  -2.00   0.50   10.00    --   10.07 -38.00 120.00  102
;
_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      0.0281131000
_diffrn_orient_matrix_UB_12      -0.0287202000
_diffrn_orient_matrix_UB_13      -0.0349767000
_diffrn_orient_matrix_UB_21      0.0338158000
_diffrn_orient_matrix_UB_22      -0.0386727000
_diffrn_orient_matrix_UB_23      0.0344717000
_diffrn_orient_matrix_UB_31      -0.0362589000
_diffrn_orient_matrix_UB_32      -0.0291015000
_diffrn_orient_matrix_UB_33      0.0162747000
_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  0.0711
_diffrn_reflns_av_unetI/netI     0.0879
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31894
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.136
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57670
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.035
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0022(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     657
_refine_ls_number_reflns         9969
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1444
_refine_ls_R_factor_gt           0.0804
_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^)+(0.1249P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2125
_refine_ls_wR_factor_ref         0.2531
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5099
_reflns_number_total             9969
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04870a2.cif
_cod_data_source_block           iiserm-928
_cod_database_code               7130923
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 99.50
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C40A, C40B}
{C43A, C43B}
3. Uiso/Uaniso restraints and constraints
Uanis(C40A) = Uanis(C40B)
Uanis(C43A) = Uanis(C43B)
4. Others
 Sof(H41A)=Sof(H48A)=Sof(H44A)=Sof(C40B)=Sof(C43B)=Sof(N5B)=Sof(N6B)=1-FVAR(1)
 Sof(N5A)=Sof(C40A)=Sof(H41)=Sof(N6A)=Sof(C43A)=Sof(H48)=Sof(H44)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C30(H30), C33(H33), C32(H32)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C35(H35A,H35B)
5.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C10(H10), C11(H11), C14(H14), C41(H41), C41(H41A), C20(H20),
 C42(H42), C18(H18), C26(H26), C19(H19), C23(H23), C54(H54), C38(H38), C39(H39),
  C46(H46), C16(H16), C48(H48), C48(H48A), C25(H25), C53(H53), C24(H24),
 C17(H17), C47(H47), C45(H45), C44(H44), C44(H44A), C51(H51), C52(H52)
5.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C1(H1A,H1B,H1C), C36(H36A,H36B,H36C), C8(H8A,H8B,H8C),
 C29(H29A,H29B,H29C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              42396
_shelx_hkl_checksum              50935
_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 1.851
_oxdiff_exptl_absorpt_empirical_full_min 0.617