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#$Date: 2021-06-05 21:07:32 +0300 (Sat, 05 Jun 2021) $
#$Revision: 265942 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/25/7242579.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7242579
loop_
_publ_author_name
'Reason, Thomas E.'
'Goka, Benjamin'
'Krause, Jeanette A.'
'Fionah, Abelline K.'
'Zahran, Elsayed M.'
'Rayat, Sundeep'
_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         'C13 H9 F N4 O'
_chemical_formula_sum            'C13 H9 F N4 O'
_chemical_formula_weight         256.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4264(4)
_cell_length_b                   26.8268(16)
_cell_length_c                   5.6645(3)
_cell_measurement_reflns_used    9097
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.41
_cell_measurement_theta_min      3.29
_cell_volume                     1128.52(11)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon-II'
_diffrn_measurement_method       'ω-φ scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            30973
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.615
_diffrn_reflns_theta_min         6.600
_diffrn_source                   'Incoatec Cu-microfocus 3.0'
_exptl_absorpt_coefficient_mu    0.946
_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    1.508
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0325
_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/[σ²(Fo²)+(0.0305P)²+0.4109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0799
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1061
_reflns_number_total             1144
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00119a2.cif
_cod_data_source_block           1ad
_cod_depositor_comments
'Adding full bibliography for 7242574--7242580.cif.'
_cod_database_code               7242579
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.828
_shelx_estimated_absorpt_t_max   0.952
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.26101(17) 0.250000 0.2622(2) 0.0376(3) Uani 1 2 d S T P . .
N1 N 0.44526(12) 0.28987(4) 0.54121(16) 0.0279(2) Uani 1 1 d . . . . .
N2 N 0.55963(14) 0.27373(4) 0.71365(19) 0.0357(3) Uani 1 1 d . . . . .
F1 F 0.2873(2) 0.48642(5) 0.4569(3) 0.0435(4) Uani 0.5 1 d . . P A 1
C1 C 0.3687(2) 0.250000 0.4242(3) 0.0278(3) Uani 1 2 d S T P . .
C2 C 0.40794(14) 0.34146(4) 0.51541(19) 0.0278(3) Uani 1 1 d . . . . .
C3 C 0.31934(15) 0.35866(5) 0.3148(2) 0.0323(3) Uani 1 1 d . . . . .
H3 H 0.286373 0.336209 0.192508 0.039 Uiso 1 1 calc R U . . .
C4 C 0.27986(16) 0.40900(5) 0.2959(2) 0.0349(3) Uani 1 1 d . . . . .
H4 H 0.218110 0.421234 0.160925 0.042 Uiso 1 1 calc R U . . .
C5 C 0.33022(16) 0.44123(5) 0.4729(2) 0.0369(3) Uani 1 1 d . . . . .
H5 H 0.302660 0.475676 0.458446 0.044 Uiso 0.5 1 calc R U P A 2
C6 C 0.42010(16) 0.42448(5) 0.6711(2) 0.0349(3) Uani 1 1 d . . . . .
H6 H 0.454946 0.447286 0.791035 0.042 Uiso 1 1 calc R U . . .
C7 C 0.45904(15) 0.37423(5) 0.6939(2) 0.0313(3) Uani 1 1 d . . . . .
H7 H 0.520027 0.362227 0.829891 0.038 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 110.73(10) . . ?
N2 N1 C2 120.32(9) . . ?
C1 N1 C2 128.72(10) . . ?
N2 N2 N1 108.50(6) 7_565 . ?
O1 C1 N1 129.23(6) . 7_565 ?
O1 C1 N1 129.23(6) . . ?
N1 C1 N1 101.53(13) 7_565 . ?
C3 C2 C7 120.81(11) . . ?
C3 C2 N1 119.99(10) . . ?
C7 C2 N1 119.19(10) . . ?
C4 C3 C2 119.08(11) . . ?
C5 C4 C3 119.91(11) . . ?
F1 C5 C4 119.00(13) . . ?
F1 C5 C6 119.65(14) . . ?
C4 C5 C6 121.29(12) . . ?
C5 C6 C7 119.54(12) . . ?
C6 C7 C2 119.36(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.217(2) . ?
N1 N2 1.3650(13) . ?
N1 C1 1.3810(14) . ?
N1 C2 1.4188(15) . ?
N2 N2 1.273(2) 7_565 ?
F1 C5 1.2568(19) . ?
C2 C3 1.3919(16) . ?
C2 C7 1.3924(16) . ?
C3 C4 1.3862(18) . ?
C4 C5 1.3755(18) . ?
C5 C6 1.3816(18) . ?
C6 C7 1.3849(18) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 N2 -0.25(10) . . . 7_565 ?
C2 N1 N2 N2 174.69(7) . . . 7_565 ?
N2 N1 C1 O1 179.84(15) . . . . ?
C2 N1 C1 O1 5.4(2) . . . . ?
N2 N1 C1 N1 0.37(15) . . . 7_565 ?
C2 N1 C1 N1 -174.03(7) . . . 7_565 ?
N2 N1 C2 C3 168.00(10) . . . . ?
C1 N1 C2 C3 -18.07(18) . . . . ?
N2 N1 C2 C7 -12.76(15) . . . . ?
C1 N1 C2 C7 161.17(12) . . . . ?
C7 C2 C3 C4 -0.94(17) . . . . ?
N1 C2 C3 C4 178.29(10) . . . . ?
C2 C3 C4 C5 0.78(18) . . . . ?
C3 C4 C5 F1 -177.31(13) . . . . ?
C3 C4 C5 C6 -0.02(19) . . . . ?
F1 C5 C6 C7 176.67(13) . . . . ?
C4 C5 C6 C7 -0.60(19) . . . . ?
C5 C6 C7 C2 0.44(17) . . . . ?
C3 C2 C7 C6 0.33(17) . . . . ?
N1 C2 C7 C6 -178.91(10) . . . . ?
