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_7158703
_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         'C36 H30 N4 O3'
_chemical_formula_sum            'C36 H30 N4 O3'
_chemical_formula_weight         566.64
_chemical_name_systematic        C36H30N4O3
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 99.768(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0633(6)
_cell_length_b                   18.6689(10)
_cell_length_c                   14.5350(8)
_cell_measurement_reflns_used    2258
_cell_measurement_temperature    296.0
_cell_measurement_theta_max      22.5680
_cell_measurement_theta_min      2.6320
_cell_volume                     2958.5(3)
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.885
_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    -56.00 -30.00   0.50    7.50    --   29.89  54.00 -30.00   52
  2  \w     40.00  67.00   0.50    7.50    --   29.89  54.00 -30.00   54
  3  \w    -68.00 116.00   0.50    7.50    --   29.89  54.00 150.00  368
;
_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      -0.0596355000
_diffrn_orient_matrix_UB_12      0.0014922000
_diffrn_orient_matrix_UB_13      -0.0271088000
_diffrn_orient_matrix_UB_21      -0.0255148000
_diffrn_orient_matrix_UB_22      -0.0114853000
_diffrn_orient_matrix_UB_23      0.0391102000
_diffrn_orient_matrix_UB_31      -0.0055732000
_diffrn_orient_matrix_UB_32      0.0361752000
_diffrn_orient_matrix_UB_33      0.0135727000
_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  0.0314
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17415
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.725
_diffrn_reflns_theta_min         2.532
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99667
_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 dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         9634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1806
_refine_ls_R_factor_gt           0.0775
_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^)+(0.1269P)^2^+0.1864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2018
_refine_ls_wR_factor_ref         0.2813
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3860
_reflns_number_total             9634
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00658h2.cif
_cod_data_source_block           rd134
_cod_database_code               7158703
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.972
_reflns_odcompleteness_completeness 99.85
_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 C(H,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:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C36(H36), C8(H8), C21(H21), C30(H30), C25(H25), C33(H33), C26(H26),
 C9(H9), C10(H10), C12(H12), C20(H20), C18(H18), C13(H13), C14(H14), C32(H32),
 C31(H31), C19(H19)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              10291
_olex2_submission_original_sample_id 'rd 134'
_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 1.038
_oxdiff_exptl_absorpt_empirical_full_min 0.963