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_7132282
_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_absolute_configuration unk
_chemical_formula_moiety         'C10 H9 N O2'
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.188
_chemical_name_systematic        'AB 03 435'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2022-10-19 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.468(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0202(4)
_cell_length_b                   29.187(2)
_cell_length_c                   5.9119(5)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      66.537
_cell_measurement_theta_min      7.620
_cell_volume                     851.82(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      100.00
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.9809
_diffrn_measured_fraction_theta_max 0.9803
_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  0.0503
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.9809
_diffrn_reflns_Laue_measured_fraction_max 0.9803
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            25396
_diffrn_reflns_point_group_measured_fraction_full 0.9755
_diffrn_reflns_point_group_measured_fraction_max 0.9745
_diffrn_reflns_theta_full        66.6018
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         7.62
_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    0.792
_exptl_absorpt_correction_T_max  0.5842
_exptl_absorpt_correction_T_min  0.4300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1300 before and 0.0893 after correction.
The Ratio of minimum to maximum transmission is 0.7360.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             369.258
_exptl_crystal_preparation       'SLOW EVAPORATION'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.3535
_refine_diff_density_min         -0.2399
_refine_diff_density_rms         0.0603
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_d_res_high            0.8400
_refine_ls_d_res_low             5.8135
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0434
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     240
_refine_ls_number_reflns         2910
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0434
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0949P)^2^+0.7349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1568
_refine_ls_wR_factor_ref         0.1568
_reflns_Friedel_coverage         0.969
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              34
_reflns_limit_k_min              -34
_reflns_limit_l_max              7
_reflns_limit_l_min              -7
_reflns_number_gt                2905
_reflns_number_total             2910
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cc04443b2.cif
_cod_data_source_block           AB_03_435_0m_a
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C20 H18 N2 O4'
_cod_original_formula_weight         350.377
_cod_original_formula_moiety         '2(C10 H9 N O2)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        851.83(12)
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               7132282
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C13(H13), C2(H2), C6(H6), C16(H16), C17(H17), C19(H19),
 C5(H5), C18(H18)
2.b Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c), C9(H9a,H9b,H9c)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_olex2_submission_original_sample_id 'AB 03 435'
_olex2_submission_special_instructions 'No special instructions were received'