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#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/25/7242578.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_7242578
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         'C15 H13 N5 O5'
_chemical_formula_sum            'C15 H13 N5 O5'
_chemical_formula_weight         343.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 102.3008(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.8994(2)
_cell_length_b                   21.1784(11)
_cell_length_c                   8.9913(5)
_cell_measurement_reflns_used    9854
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.38
_cell_measurement_theta_min      2.38
_cell_volume                     725.48(7)
_computing_cell_refinement       'Bruker SAINT v8.38A'
_computing_data_collection       'Bruker APEX3 v2016.9.0'
_computing_data_reduction        'Bruker SAINT v8.38A'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material
'Bruker SHELXTL v6.14 & SHELXL-2017/1 (Sheldrick, 2014)'
_computing_structure_refinement
'Bruker SHELXTL v6.14 & SHELXL-2017/1 (Sheldrick, 2014)'
_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 PHOTON_II'
_diffrn_measurement_method       'combination of ω and φ-scans'
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7288
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21425
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.930
_diffrn_reflns_theta_max         31.399
_diffrn_reflns_theta_min         2.377
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.711
_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    1.572
_exptl_crystal_description       needle
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.074
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       0.055(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4367
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0410
_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)+(0.0489P)²+0.0818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0913
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                4125
_reflns_number_total             4367
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00119a2.cif
_cod_data_source_block           1cl
_cod_depositor_comments
'Adding full bibliography for 7242574--7242580.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7242578
_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   0.991
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.4967(4) 0.54613(6) 0.31576(16) 0.0282(3) Uani 1 1 d . . . . .
O2 O 1.1368(4) 0.72496(6) 0.60274(15) 0.0279(3) Uani 1 1 d . . . . .
O3 O 1.6614(4) 0.57264(7) 0.97086(15) 0.0271(3) Uani 1 1 d . . . . .
O4 O -0.4397(5) 0.34813(9) -0.2405(2) 0.0456(5) Uani 1 1 d . . . . .
O5 O -0.3421(5) 0.25953(8) -0.1220(2) 0.0441(4) Uani 1 1 d . . . . .
N1 N 0.6128(4) 0.43778(7) 0.35248(17) 0.0212(3) Uani 1 1 d . . . . .
N2 N 0.8315(5) 0.40256(8) 0.4609(2) 0.0281(4) Uani 1 1 d . . . . .
N3 N 1.0105(5) 0.44035(8) 0.55756(19) 0.0279(4) Uani 1 1 d . . . . .
N4 N 0.9145(4) 0.50105(7) 0.51601(17) 0.0207(3) Uani 1 1 d . . . . .
N5 N -0.2946(5) 0.31621(9) -0.1324(2) 0.0288(4) Uani 1 1 d . . . . .
C1 C 0.6534(5) 0.50210(8) 0.3842(2) 0.0202(3) Uani 1 1 d . . . . .
C2 C 0.3824(5) 0.40781(8) 0.2295(2) 0.0205(3) Uani 1 1 d . . . . .
C3 C 0.2324(5) 0.44250(9) 0.1003(2) 0.0243(4) Uani 1 1 d . . . . .
H3 H 0.281877 0.486212 0.093857 0.029 Uiso 1 1 calc R U . . .
C4 C 0.0093(5) 0.41194(9) -0.0187(2) 0.0246(4) Uani 1 1 d . . . . .
H4 H -0.097567 0.434593 -0.107774 0.030 Uiso 1 1 calc R U . . .
C5 C -0.0560(5) 0.34816(9) -0.0065(2) 0.0227(4) Uani 1 1 d . . . . .
C6 C 0.0931(5) 0.31339(9) 0.1219(2) 0.0256(4) Uani 1 1 d . . . . .
H6 H 0.043311 0.269657 0.127661 0.031 Uiso 1 1 calc R U . . .
C7 C 0.3154(5) 0.34347(8) 0.2412(2) 0.0242(4) Uani 1 1 d . . . . .
H7 H 0.421145 0.320616 0.330073 0.029 Uiso 1 1 calc R U . . .
C8 C 1.0775(5) 0.55253(8) 0.60658(19) 0.0200(3) Uani 1 1 d . . . . .
C9 C 1.2966(5) 0.53902(8) 0.7454(2) 0.0218(3) Uani 1 1 d . . . . .
H9 H 1.338888 0.496647 0.778935 0.026 Uiso 1 1 calc R U . . .
C10 C 1.4544(5) 0.58956(9) 0.8350(2) 0.0217(3) Uani 1 1 d . . . . .
C11 C 1.3933(5) 0.65143(9) 0.7856(2) 0.0226(4) Uani 1 1 d . . . . .
H11 H 1.498004 0.685563 0.847530 0.027 Uiso 1 1 calc R U . . .
C12 C 1.1747(5) 0.66278(8) 0.6430(2) 0.0210(3) Uani 1 1 d . . . . .
C13 C 1.0120(5) 0.61395(8) 0.5514(2) 0.0210(3) Uani 1 1 d . . . . .
H13 H 0.862447 0.621991 0.455138 0.025 Uiso 1 1 calc R U . . .
C14 C 0.9200(6) 0.73968(10) 0.4568(2) 0.0294(4) Uani 1 1 d . . . . .
H14A H 0.922477 0.785369 0.439784 0.044 Uiso 1 1 calc R U . . .
H14B H 0.678949 0.725801 0.453948 0.044 Uiso 1 1 calc R U . . .
H14C H 1.010598 0.717909 0.376956 0.044 Uiso 1 1 calc R U . . .
C15 C 1.8314(5) 0.62246(10) 1.0678(2) 0.0271(4) Uani 1 1 d . . . . .
H15A H 1.979702 0.604194 1.159458 0.041 Uiso 1 1 calc R U . . .
H15B H 1.653516 0.649759 1.096805 0.041 Uiso 1 1 calc R U . . .
H15C H 1.976836 0.647408 1.013190 0.041 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 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0115 0.0064 '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
C12 O2 C14 117.46(14) . . ?
C10 O3 C15 117.36(15) . . ?
N2 N1 C1 111.11(14) . . ?
N2 N1 C2 120.38(14) . . ?
C1 N1 C2 128.50(15) . . ?
N3 N2 N1 108.09(14) . . ?
N2 N3 N4 108.99(15) . . ?
N3 N4 C1 110.87(15) . . ?
N3 N4 C8 119.96(14) . . ?
C1 N4 C8 129.16(15) . . ?
O4 N5 O5 123.62(18) . . ?
O4 N5 C5 117.97(17) . . ?
O5 N5 C5 118.40(18) . . ?
O1 C1 N4 130.25(17) . . ?
O1 C1 N1 128.82(16) . . ?
N4 C1 N1 100.92(14) . . ?
C3 C2 C7 121.68(17) . . ?
C3 C2 N1 119.87(15) . . ?
C7 C2 N1 118.45(16) . . ?
C4 C3 C2 118.70(16) . . ?
C5 C4 C3 119.34(17) . . ?
C4 C5 C6 122.17(17) . . ?
C4 C5 N5 119.08(17) . . ?
C6 C5 N5 118.74(16) . . ?
C7 C6 C5 118.89(17) . . ?
C6 C7 C2 119.21(17) . . ?
C9 C8 C13 122.97(16) . . ?
C9 C8 N4 118.11(15) . . ?
C13 C8 N4 118.91(15) . . ?
C8 C9 C10 118.18(16) . . ?
O3 C10 C11 124.38(17) . . ?
O3 C10 C9 114.78(16) . . ?
C11 C10 C9 120.84(16) . . ?
C10 C11 C12 118.99(16) . . ?
O2 C12 C13 123.42(16) . . ?
O2 C12 C11 114.75(16) . . ?
C13 C12 C11 121.83(16) . . ?
C12 C13 C8 117.18(15) . . ?
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 1.209(2) . ?
O2 C12 1.366(2) . ?
O2 C14 1.436(2) . ?
O3 C10 1.361(2) . ?
O3 C15 1.437(2) . ?
O4 N5 1.220(2) . ?
O5 N5 1.221(2) . ?
N1 N2 1.371(2) . ?
N1 C1 1.394(2) . ?
N1 C2 1.417(2) . ?
N2 N3 1.275(2) . ?
N3 N4 1.368(2) . ?
N4 C1 1.389(2) . ?
N4 C8 1.426(2) . ?
N5 C5 1.468(2) . ?
C2 C3 1.394(2) . ?
C2 C7 1.396(2) . ?
C3 C4 1.387(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.388(3) . ?
C6 C7 1.383(3) . ?
C8 C9 1.384(2) . ?
C8 C13 1.396(2) . ?
C9 C10 1.401(2) . ?
C10 C11 1.388(2) . ?
C11 C12 1.401(2) . ?
C12 C13 1.389(2) . ?
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 N3 -0.9(2) . . . . ?
C2 N1 N2 N3 179.78(17) . . . . ?
N1 N2 N3 N4 0.2(2) . . . . ?
N2 N3 N4 C1 0.6(2) . . . . ?
N2 N3 N4 C8 179.88(16) . . . . ?
N3 N4 C1 O1 177.7(2) . . . . ?
C8 N4 C1 O1 -1.5(3) . . . . ?
N3 N4 C1 N1 -1.03(19) . . . . ?
C8 N4 C1 N1 179.75(16) . . . . ?
N2 N1 C1 O1 -177.6(2) . . . . ?
C2 N1 C1 O1 1.7(3) . . . . ?
N2 N1 C1 N4 1.1(2) . . . . ?
C2 N1 C1 N4 -179.59(17) . . . . ?
N2 N1 C2 C3 -162.83(17) . . . . ?
C1 N1 C2 C3 18.0(3) . . . . ?
N2 N1 C2 C7 16.4(3) . . . . ?
C1 N1 C2 C7 -162.78(18) . . . . ?
C7 C2 C3 C4 0.4(3) . . . . ?
N1 C2 C3 C4 179.65(18) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C5 N5 179.48(17) . . . . ?
O4 N5 C5 C4 -3.4(3) . . . . ?
O5 N5 C5 C4 177.91(19) . . . . ?
O4 N5 C5 C6 175.76(19) . . . . ?
O5 N5 C5 C6 -3.0(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
N5 C5 C6 C7 -179.38(18) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
C3 C2 C7 C6 -0.3(3) . . . . ?
N1 C2 C7 C6 -179.56(17) . . . . ?
N3 N4 C8 C9 -8.3(2) . . . . ?
C1 N4 C8 C9 170.86(17) . . . . ?
N3 N4 C8 C13 171.18(17) . . . . ?
C1 N4 C8 C13 -9.7(3) . . . . ?
C13 C8 C9 C10 1.1(3) . . . . ?
N4 C8 C9 C10 -179.46(16) . . . . ?
C15 O3 C10 C11 -1.0(3) . . . . ?
C15 O3 C10 C9 179.84(17) . . . . ?
C8 C9 C10 O3 178.95(16) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
O3 C10 C11 C12 179.95(18) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C14 O2 C12 C13 -0.8(3) . . . . ?
C14 O2 C12 C11 179.10(17) . . . . ?
C10 C11 C12 O2 -178.53(18) . . . . ?
C10 C11 C12 C13 1.4(3) . . . . ?
O2 C12 C13 C8 179.35(18) . . . . ?
C11 C12 C13 C8 -0.5(3) . . . . ?
C9 C8 C13 C12 -0.7(3) . . . . ?
N4 C8 C13 C12 179.84(16) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168342106
