Iron Nitrate-Mediated Selective Synthesis of 3-Acyl-1,2,4-Oxadiazoles from Alkynes and Nitriles: The Dual Roles of Iron Nitrate.
Bian, Qilong; Wu, Cunluo; Yuan, Jiangpei; Shi, Zuodong; Ding, Tao; Huang, Yongwei; Xu, Yuanqing; Xu, Hao; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03070

data_4037911
_publ_section_title
;
 Iron Nitrate-Mediated Selective Synthesis of 3-Acyl-1,2,4-Oxadiazoles
 from Alkynes and Nitriles: The Dual Roles of Iron Nitrate.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03070
_journal_year                    2020
_chemical_formula_moiety         'C15 H10 N2 O2'
_chemical_formula_sum            'C15 H10 N2 O2'
_chemical_formula_weight         250.25
_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             2019-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.195(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.947(6)
_cell_length_b                   21.64(3)
_cell_length_c                   11.754(14)
_cell_measurement_reflns_used    1223
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      20.136
_cell_measurement_theta_min      2.578
_cell_volume                     1238(3)
_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      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'X-ray single crystal diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7852
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.399
_diffrn_reflns_theta_min         1.882
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0516 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.9104.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.0509
_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^)+(0.0558P)^2^+0.0999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1404
_reflns_number_total             2931
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03070_si_002.cif
_cod_data_source_block           mpt11761_0m
_cod_database_code               4037911
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C005, C006
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J)
;
_shelx_res_checksum              85881
_shelx_hkl_checksum              20731
_olex2_submission_original_sample_id xh
_olex2_submission_special_instructions 'No special instructions were received'