Cu2O nanoparticle-catalyzed synthesis of diaryl tetrazolones and investigation of their solid-state properties
Reason, Thomas E.; Goka, Benjamin; Krause, Jeanette A.; Fionah, Abelline K.; Zahran, Elsayed M.; Rayat, Sundeep; CrystEngComm 23 (2021) 3220–3229; doi:10.1039/D1CE00119A

data_7242580
_publ_section_title
;
 Cu2O nanoparticle-catalyzed synthesis of diaryl tetrazolones and
 investigation of their solid-state properties
;
_journal_issue                   17
_journal_name_full               CrystEngComm
_journal_page_first              3220
_journal_page_last               3229
_journal_paper_doi               10.1039/D1CE00119A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C14 H11 F N4 O2'
_chemical_formula_sum            'C14 H11 F N4 O2'
_chemical_formula_weight         286.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-12-23 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.226(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.9051(18)
_cell_length_b                   3.9102(2)
_cell_length_c                   11.6155(7)
_cell_measurement_reflns_used    9097
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.41
_cell_measurement_theta_min      3.29
_cell_volume                     1246.97(13)
_computing_cell_refinement       'Bruker SAINT v8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker APEX3 v2018.1.0 (Bruker, 2018)'
_computing_data_reduction        'Bruker SAINT v8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'
_computing_structure_refinement
'SHELXL-2017/1 (Sheldrick, 2017, G.M. Sheldrick (2015) Acta Cryst., C71, 3-8)'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon-II'
_diffrn_measurement_method       '\w-\f scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.346
_diffrn_reflns_theta_min         2.706
_diffrn_source                   'Incoatec Mo-microfocus 3.0'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS 2016/2 (L.Krause, et al. J. Appl. Cryst. (2015), 48, 3-10)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

Excerpt from refinement output:

 Flack x =   -0.223(947) by classical fit to all intensities
              0.278(236) from 1249 selected quotients (Parsons' method)

 ** Absolute structure cannot be determined reliably **
;
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0286
_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^)+(0.0419P)^2^+0.3493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0755
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3004
_reflns_number_total             3123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00119a2.cif
_cod_data_source_block           1beMeOH
_cod_depositor_comments
'Adding full bibliography for 7242574--7242580.cif.'
_cod_original_cell_volume        1246.98(13)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7242580
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              13255