EDA complex-mediated [3 + 2] cyclization for the synthesis of CF3-oxadiazoles
Huang, Mengjun; Wang, Guoqiang; Li, Heyin; Zou, Zhenlei; Jia, Xingye; Karotsis, Georgios; Pan, Yi; Zhang, Weigang; Ma, Jing; Wang, Yi; Green Chemistry 27 (2025) 413–419; doi:10.1039/D4GC05267F

data_7249639
_publ_section_title
;
 EDA complex-mediated [3 + 2] cyclization for the synthesis of
 CF3-oxadiazoles
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              413
_journal_page_last               419
_journal_paper_doi               10.1039/D4GC05267F
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         '2(C10 H8 F3 N3 O)'
_chemical_formula_sum            'C20 H16 F6 N6 O2'
_chemical_formula_weight         486.39
_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     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2g0n27
_audit_creation_date             2023-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-05-23 deposited with the CCDC.	2024-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.113(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.900(3)
_cell_length_b                   12.748(6)
_cell_length_c                   28.745(15)
_cell_measurement_reflns_used    4557
_cell_measurement_temperature    193.0
_cell_measurement_theta_max      48.09
_cell_measurement_theta_min      2.69
_cell_volume                     2153.4(19)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      193.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            26562
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.972
_diffrn_reflns_theta_min         2.685
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.5961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1383 before and 0.0899 after correction.
The Ratio of minimum to maximum transmission is 0.7942.
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    1.500
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0641
_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^)+(0.0901P)^2^+0.3134P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2396
_reflns_number_total             3932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc05267f2.cif
_cod_data_source_block           hmj_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7249639.cif.
;
_cod_original_cell_volume        2153.3(19)
_cod_database_code               7249639
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.927
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4A), C6(H6), C12(H12), C2(H2), C3(H3), C16(H16), C5(H5), C4(H4),
 C13(H13), C14(H14), C15(H15)
;
_shelx_res_checksum              48736
_shelx_hkl_checksum              20156
_olex2_submission_special_instructions 'No special instructions were received'