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_7132287
_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         'C17 H20 N2 O2'
_chemical_formula_sum            'C17 H20 N2 O2'
_chemical_formula_weight         284.35
_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             2022-09-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-10-19 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                81.9570(10)
_cell_angle_beta                 78.9680(10)
_cell_angle_gamma                70.0130(10)
_cell_formula_units_Z            4
_cell_length_a                   10.1881(4)
_cell_length_b                   11.1979(4)
_cell_length_c                   13.8192(5)
_cell_measurement_reflns_used    9805
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      65.014
_cell_measurement_theta_min      6.109
_cell_volume                     1449.48(9)
_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    'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_publication_material  'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick 2018)'
_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 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX3_IMuS Diamond_Photon III'
_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  0.0616
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            49799
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        65.009
_diffrn_reflns_theta_max         65.009
_diffrn_reflns_theta_min         6.109
_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    0.689
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1350 before and 0.0903 after correction. The Ratio of minimum to maximum transmission is 0.6956. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.405
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.109(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         4716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0755P)^2^+0.5229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4644
_reflns_number_total             4716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04443b2.cif
_cod_data_source_block           ab_05_814_2_0m_a
_cod_depositor_comments
;

2024-11-09
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C34 H40 N4 O4'
_cod_original_formula_weight         568.70
_cod_original_formula_moiety         '2(C17 H20 N2 O2)'
_cod_original_formula_units_Z            2
_cod_database_code               7132287
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.663
_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:
 C30(H30), C10(H10), C13(H13), C16(H16), C27(H27), C33(H33)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C31(H31A,H31B), C14(H14A,H14B), C15(H15A,H15B), C28(H28A,
 H28B), C12(H12A,H12B), C29(H29A,H29B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C1(H1A), C7(H7), C6(H6), C19(H19), C22(H22), C25(H25), C4(H4),
  C5(H5), C21(H21), C20(H20)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C)
;
_olex2_submission_special_instructions 'No special instructions were received'