A Condition-Tuned Unorthodox Approach to Indole-3-Carboxylic Acids and Anthranilic Acids via Carbon Atom Translocation
Bhowmik, arup; Naskar, Koushik; Roy, Shantonu; Karmakar, Sudip; Sarkar, Writhabrata; Mondal, Imtiaj; Sana, Arindam; Deb, Indubhusan; Chemical Communications  (2023) –; doi:10.1039/D3CC04443B

data_7132286
_publ_section_title
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 A Condition-Tuned Unorthodox Approach to Indole-3-Carboxylic Acids and
 Anthranilic Acids via Carbon Atom Translocation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04443B
_journal_year                    2023
_chemical_formula_moiety         'C2 H6 O S, C36 H20 N4 O4'
_chemical_formula_sum            'C38 H26 N4 O5 S'
_chemical_formula_weight         650.69
_chemical_name_systematic        'N-CONFUSED PORPHYRIN RING'
_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             2022-10-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2022-10-19 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.515(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3315(10)
_cell_length_b                   7.6770(5)
_cell_length_c                   25.9418(17)
_cell_measurement_reflns_used    9071
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      65.01
_cell_measurement_theta_min      5.81
_cell_volume                     3033.6(3)
_computing_cell_refinement       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2(Sheldrick 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX3_IMuS Diamond_Photon III (1)'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            44102
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        65.176
_diffrn_reflns_theta_max         65.176
_diffrn_reflns_theta_min         5.809
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.400
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1042 before and 0.0688 after correction. The Ratio of minimum to maximum transmission is 0.8863. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1352
_exptl_crystal_preparation       'IN DMSO'
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION OF DMSO'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0720P)^2^+2.8860P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1359
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4942
_reflns_number_total             5057
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04443b2.cif
_cod_data_source_block           ab_05_814_0m_a
_cod_database_code               7132286
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.787
_shelx_estimated_absorpt_t_min   0.640
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27), C30(H30),
  C31(H31), C32(H32), C33(H33), C36(H36)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              33656
_shelx_hkl_checksum              27087
_olex2_submission_special_instructions 'No special instructions were received'