Practical scale up synthesis of carboxylic acids and their bioisosteres 5-substituted-1H-tetrazoles catalyzed by a graphene oxide-based solid acid carbocatalyst
Mittal, Rupali; Kumar, Amit; Awasthi, Satish Kumar; RSC Advances 11 (2021) 11166–11176; doi:10.1039/D1RA01053K

data_7242416
_publ_section_title
;
 Practical scale up synthesis of carboxylic acids and their bioisosteres
 5-substituted-1H-tetrazoles catalyzed by a graphene oxide-based solid
 acid carbocatalyst
;
_journal_issue                   19
_journal_name_full               'RSC Advances'
_journal_page_first              11166
_journal_page_last               11176
_journal_paper_doi               10.1039/D1RA01053K
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C8 H7 Cl N4'
_chemical_formula_sum            'C8 H7 Cl N4'
_chemical_formula_weight         194.63
_chemical_name_systematic        5-(3-chlorobenzyl)-1H-tetrazole
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-09-14 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.575(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8058(5)
_cell_length_b                   26.6823(19)
_cell_length_c                   7.1899(7)
_cell_measurement_reflns_used    2632
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4860
_cell_measurement_theta_min      3.7240
_cell_volume                     883.65(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9853
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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      0.00  87.00   1.00    2.50    --   18.84  57.00   0.00   87
  2  \w      6.00  87.00   1.00    2.50    --   18.84  57.00 -90.00   81
  3  \w    -25.00  59.00   1.00    2.50    --   18.84 -99.00 -60.00   84
  4  \w    -25.00  59.00   1.00    2.50    --   18.84 -99.00-150.00   84
  5  \w    -48.00  35.00   1.00    2.50    --   18.84 -57.00   0.00   83
  6  \w    -25.00  59.00   1.00    2.50    --   18.84 -99.00 120.00   84
  7  \w     -6.00  82.00   1.00    2.50    --   18.84  77.00 150.00   88
  8  \w    -82.00  -1.00   1.00    2.50    --  -15.17 -57.00  30.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0782383000
_diffrn_orient_matrix_UB_12      0.0220179000
_diffrn_orient_matrix_UB_13      -0.0381814000
_diffrn_orient_matrix_UB_21      0.1269001000
_diffrn_orient_matrix_UB_22      0.0145769000
_diffrn_orient_matrix_UB_23      0.0386433000
_diffrn_orient_matrix_UB_31      0.0383747000
_diffrn_orient_matrix_UB_32      -0.0031717000
_diffrn_orient_matrix_UB_33      -0.0874456000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11098
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.327
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.386
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate: Hexane (1:1)'
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0718
_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^)+(0.0319P)^2^+1.0298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1463
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1379
_reflns_number_total             1617
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra01053k2.cif
_cod_data_source_block           c
_cod_database_code               7242416
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C8 H7 Cl N4'
_chemical_oxdiff_usercomment     28-08-2019
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C4(H4A)
;
_shelx_res_checksum              9975
_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 1.610
_oxdiff_exptl_absorpt_empirical_full_min 0.591