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_7132285
_publ_section_title
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 A Condition-Tuned Unorthodox Approach to Indole-3-Carboxylic Acids and
 Anthranilic Acids via Carbon Atom Translocation
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04443B
_journal_year                    2023
_chemical_formula_moiety         'C9 H10 Cl N O2'
_chemical_formula_sum            'C9 H10 Cl N O2'
_chemical_formula_weight         199.63
_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             2022-05-26
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
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2022-10-19 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.433(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8685(6)
_cell_length_b                   7.0616(5)
_cell_length_c                   16.2493(12)
_cell_measurement_reflns_used    9313
_cell_measurement_temperature    113.00
_cell_measurement_theta_max      64.95
_cell_measurement_theta_min      5.09
_cell_volume                     902.60(12)
_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      113.00
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_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  0.0541
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9965
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        65.089
_diffrn_reflns_theta_max         65.089
_diffrn_reflns_theta_min         8.317
_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    3.473
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1289 before and 0.0886 after correction.
The Ratio of minimum to maximum transmission is 0.6961.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.441
_refine_diff_density_min         -1.013
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.245
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.245
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0730P)^2^+0.5696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1475
_reflns_number_total             1481
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04443b2.cif
_cod_data_source_block           ab_04_667_2_0m_a
_cod_database_code               7132285
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.337
_shelx_estimated_absorpt_t_min   0.276
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2A), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'