Silver - Catalyzed Decarboxylative Cyclization for the Synthesis of Substituted Pyrazoles from 1,2-Diaza-1,3-dienes and α-Keto Acids
Katiyar, Sarita; Kumar, Abhishek; Koneni, Sashidhara Sashidhara; Chemical Communications  (2022) –; doi:10.1039/D2CC01793H

data_7130159
_publ_section_title
;
 Silver - Catalyzed Decarboxylative Cyclization for the Synthesis of
 Substituted Pyrazoles from 1,2-Diaza-1,3-dienes and \a-Keto Acids
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01793H
_journal_year                    2022
_chemical_formula_moiety         'C17 H13 N3'
_chemical_formula_sum            'C17 H13 N3'
_chemical_formula_weight         259.30
_chemical_name_systematic        23maya1
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-28 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.488(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.011(3)
_cell_length_b                   7.5421(9)
_cell_length_c                   18.744(2)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.43
_cell_volume                     2658.5(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         2.910
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7062
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1235 before and 0.0539 after correction. The Ratio of minimum to maximum transmission is 0.9470. 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    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0140(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         4624
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0163P)^2^+2.6209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4408
_reflns_number_total             4624
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01793h2.cif
_cod_data_source_block           notwin
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_ambient_temperature' value '100 (2)' was changed
to '100(2)' -- the value was reformatted.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7130159
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.984
_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:
 C7(H7), C11A(H11A), C7A(H7A), C11(H11), C13A(H13A), C8A(H8A), C13(H13),
 C9A(H9A), C17A(H17A), C16A(H16A), C10(H10), C10A(H10A), C9(H9), C8(H8),
 C17(H17), C15(H15), C14(H14), C15A(H15A), C14A(H14A), C16(H16)
2.b Idealised Me refined as rotating group:
 C4A(H4AA,H4AB,H4AC), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              84806
_shelx_hkl_checksum              55500
_olex2_submission_original_sample_id 23maya1
_olex2_submission_special_instructions 'No special instructions were received'