Construction of carbazole-based unnatural amino acid scaffolds via Pd(ii)-catalyzed C(sp3)–H functionalization
Kaur, Ramandeep; Banga, Shefali; Babu, Srinivasarao Arulananda; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00658H

data_7158704
_publ_section_title
;
 Construction of carbazole-based unnatural amino acid scaffolds via
 Pd(ii)-catalyzed C(sp3)--H functionalization
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00658H
_journal_year                    2022
_chemical_formula_moiety         'C44 H30 N4 O3'
_chemical_formula_sum            'C44 H30 N4 O3'
_chemical_formula_weight         662.72
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-04-05 deposited with the CCDC.	2022-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                77.779(4)
_cell_angle_beta                 79.315(3)
_cell_angle_gamma                84.970(3)
_cell_formula_units_Z            2
_cell_length_a                   11.1250(4)
_cell_length_b                   13.0700(6)
_cell_length_c                   14.0121(6)
_cell_measurement_reflns_used    1751
_cell_measurement_temperature    296.0
_cell_measurement_theta_max      22.7670
_cell_measurement_theta_min      2.9350
_cell_volume                     1954.23(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.863
_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     24.00 119.00   0.50    5.00    --   29.89  54.00   0.00  190
  2  \w    -53.00 -27.00   0.50    5.00    --   29.89  54.00-150.00   52
  3  \w     42.00  68.00   0.50    5.00    --   29.89  54.00-150.00   52
  4  \w    -63.00 119.00   0.50    5.00    --   29.89  54.00 120.00  364
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0053014000
_diffrn_orient_matrix_UB_12      0.0544627000
_diffrn_orient_matrix_UB_13      0.0000750000
_diffrn_orient_matrix_UB_21      -0.0004860000
_diffrn_orient_matrix_UB_22      0.0110470000
_diffrn_orient_matrix_UB_23      -0.0517208000
_diffrn_orient_matrix_UB_31      -0.0647462000
_diffrn_orient_matrix_UB_32      -0.0017289000
_diffrn_orient_matrix_UB_33      0.0094217000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.1002
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16391
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.789
_diffrn_reflns_theta_min         2.593
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (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    1.126
_exptl_crystal_description       block
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         12475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.897
_refine_ls_R_factor_all          0.1838
_refine_ls_R_factor_gt           0.0744
_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^)+(0.1101P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1937
_refine_ls_wR_factor_ref         0.2895
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3673
_reflns_number_total             12475
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00658h2.cif
_cod_data_source_block           rd46
_cod_database_code               7158704
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.972
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C15(H15), C12(H12), C11(H11), C42(H42), C29(H29), C39(H39), C23(H23),
 C35(H35), C17(H17), C5(H5), C27(H27), C31(H31), C33(H33), C9(H9), C25(H25),
 C41(H41), C30(H30), C24(H24), C20(H20), C26(H26), C34(H34), C40(H40), C19(H19),
  C18(H18), C6(H6), C8(H8), C7(H7)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              7629
_shelx_fab_checksum              22719
_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 1.133
_oxdiff_exptl_absorpt_empirical_full_min 0.911