Picolinamide-assisted ortho-C–H functionalization of pyrenylglycine derivatives using aryl iodides
Dalal, Arup; Bodak, Subhankar; Babu, Srinivasarao Arulananda; Organic & Biomolecular Chemistry 22 (2024) 1279–1298; doi:10.1039/D3OB01731A

data_7159764
_publ_section_title
;
 Picolinamide-assisted ortho-C--H functionalization of pyrenylglycine
 derivatives using aryl iodides
;
_journal_issue                   6
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1279
_journal_page_last               1298
_journal_paper_doi               10.1039/D3OB01731A
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C34 H28 Br N3 O2'
_chemical_formula_sum            'C34 H28 Br N3 O2'
_chemical_formula_weight         590.50
_chemical_name_systematic        C34H28BrN3O2
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-31
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-09-12 deposited with the CCDC.	2024-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                61.325(17)
_cell_angle_beta                 89.722(15)
_cell_angle_gamma                89.850(15)
_cell_formula_units_Z            4
_cell_length_a                   9.6137(19)
_cell_length_b                   18.354(3)
_cell_length_c                   18.491(3)
_cell_measurement_reflns_used    7051
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.4440
_cell_measurement_theta_min      3.0370
_cell_volume                     2862.5(10)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.808
_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    -69.00 118.80   0.30   40.00    --   29.89  54.00-180.00  626
  2  \w    -69.00  72.00   0.30   40.00    --   29.89  54.00 -30.00  470
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0178266000
_diffrn_orient_matrix_UB_12      0.0373430000
_diffrn_orient_matrix_UB_13      -0.0359184000
_diffrn_orient_matrix_UB_21      0.0458735000
_diffrn_orient_matrix_UB_22      0.0221728000
_diffrn_orient_matrix_UB_23      0.0114560000
_diffrn_orient_matrix_UB_31      0.0551060000
_diffrn_orient_matrix_UB_32      -0.0074756000
_diffrn_orient_matrix_UB_33      -0.0223166000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.808
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24030
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.723
_diffrn_reflns_theta_min         3.028
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.472
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57875
_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            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.756
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     743
_refine_ls_number_reflns         17050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0870P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.2088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8340
_reflns_number_total             17050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01731a2.cif
_cod_data_source_block           exp_603
_cod_depositor_comments          'Adding full bibliography for 7159764.cif.'
_cod_database_code               7159764
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.591
_shelx_estimated_absorpt_t_min   0.527
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00P(H00P), C00Q(H00Q)
2.b Aromatic/amide H refined with riding coordinates:
 C00O(H00O), C00U(H00U), C00Y(H00Y), C00Z(H00Z), C012(H012), C013(H013),
 C016(H016), C017(H017), C019(H019), C01A(H01A), C01D(H01D), C01F(H01F),
 C01H(H01H), C01I(H01I), C01K(H01K), C01L(H01L), C01M(H01M), C01O(H01O),
 C01P(H01P), C01Q(H01Q), C01R(H01R), C01S(H01S), C01T(H01T), C01U(H01U),
 C01V(H01V), C01W(H01W), C01X(H01X), C01Y(H01Y), C01Z(H01Z), C021(H021),
 C023(H023), C024(H024)
2.c Idealised Me refined as rotating group:
 C020(H02A,H02B,H02C), C022(H02J,H02K,H02L), C025(H02D,H02E,H02F), C026(H02M,
 H02N,H02O), C027(H02G,H02H,H02I), C028(H02P,H02Q,H02R)
;
_shelx_res_checksum              49448
_olex2_submission_original_sample_id exp_603
_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 1.551
_oxdiff_exptl_absorpt_empirical_full_min 0.778