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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/7/24/25/7242577.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_7242577
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 H14 N4 O2'
_chemical_formula_sum            'C15 H14 N4 O2'
_chemical_formula_weight         282.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 100.713(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5655(10)
_cell_length_b                   3.9863(4)
_cell_length_c                   28.977(3)
_cell_measurement_reflns_used    7769
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.05
_cell_measurement_theta_min      2.59
_cell_volume                     1312.7(2)
_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, 2017)'
_computing_structure_refinement
'Bruker SHELXTL v6.14 & SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_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  0.0591
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            19690
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.930
_diffrn_reflns_theta_max         29.129
_diffrn_reflns_theta_min         2.128
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.623
_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    1.428
_exptl_crystal_description       blade
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.103
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0091(16)
_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   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0535P)²+0.6078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1285
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2336
_reflns_number_total             3265
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00119a2.cif
_cod_data_source_block           1bk
_cod_depositor_comments
'Adding full bibliography for 7242574--7242580.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7242577
_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   0.989
_shelx_estimated_absorpt_t_max   0.999
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.31992(10) 0.5365(3) 0.32262(4) 0.0334(3) Uani 1 1 d . . . . .
O2 O 0.37921(10) 0.3780(3) 0.09971(4) 0.0348(3) Uani 1 1 d . . . . .
N1 N 0.16036(11) 0.1960(4) 0.33314(5) 0.0273(3) Uani 1 1 d . . . . .
N2 N 0.08560(12) -0.0160(4) 0.30482(5) 0.0315(3) Uani 1 1 d . . . . .
N3 N 0.11354(12) -0.0166(4) 0.26410(5) 0.0318(3) Uani 1 1 d . . . . .
N4 N 0.20713(11) 0.1944(4) 0.26506(5) 0.0273(3) Uani 1 1 d . . . . .
C1 C 0.24095(14) 0.3365(4) 0.30896(6) 0.0270(4) Uani 1 1 d . . . . .
C2 C 0.14694(14) 0.2486(4) 0.38050(6) 0.0269(4) Uani 1 1 d . . . . .
C3 C 0.23651(14) 0.3985(4) 0.41254(6) 0.0289(4) Uani 1 1 d . . . . .
H3 H 0.306457 0.470058 0.402709 0.035 Uiso 1 1 calc R U . . .
C4 C 0.22388(15) 0.4439(4) 0.45891(6) 0.0303(4) Uani 1 1 d . . . . .
C5 C 0.12036(15) 0.3380(5) 0.47228(6) 0.0344(4) Uani 1 1 d . . . . .
H5 H 0.110605 0.367487 0.503867 0.041 Uiso 1 1 calc R U . . .
C6 C 0.03130(15) 0.1900(5) 0.44017(6) 0.0357(4) Uani 1 1 d . . . . .
H6 H -0.038722 0.119014 0.449991 0.043 Uiso 1 1 calc R U . . .
C7 C 0.04320(15) 0.1443(5) 0.39392(6) 0.0319(4) Uani 1 1 d . . . . .
H7 H -0.018064 0.044103 0.371837 0.038 Uiso 1 1 calc R U . . .
C8 C 0.25483(14) 0.2461(4) 0.22355(6) 0.0263(4) Uani 1 1 d . . . . .
C9 C 0.19185(14) 0.1316(5) 0.18090(6) 0.0304(4) Uani 1 1 d . . . . .
H9 H 0.118244 0.022749 0.179599 0.036 Uiso 1 1 calc R U . . .
C10 C 0.23684(14) 0.1769(5) 0.14045(6) 0.0319(4) Uani 1 1 d . . . . .
H10 H 0.194498 0.096011 0.111322 0.038 Uiso 1 1 calc R U . . .
C11 C 0.34393(14) 0.3403(5) 0.14206(6) 0.0286(4) Uani 1 1 d . . . . .
C12 C 0.40669(14) 0.4538(5) 0.18470(6) 0.0297(4) Uani 1 1 d . . . . .
H12 H 0.480188 0.563081 0.185948 0.036 Uiso 1 1 calc R U . . .
C13 C 0.36212(14) 0.4076(5) 0.22559(6) 0.0299(4) Uani 1 1 d . . . . .
H13 H 0.404805 0.486054 0.254793 0.036 Uiso 1 1 calc R U . . .
C14 C 0.48840(15) 0.5464(5) 0.10028(6) 0.0350(4) Uani 1 1 d . . . . .
H14A H 0.504383 0.558159 0.068273 0.052 Uiso 1 1 calc R U . . .
H14B H 0.551832 0.422822 0.120344 0.052 Uiso 1 1 calc R U . . .
H14C H 0.483949 0.774019 0.112627 0.052 Uiso 1 1 calc R U . . .
C15 C 0.32119(16) 0.6002(5) 0.49411(6) 0.0378(4) Uani 1 1 d . . . . .
H15A H 0.379736 0.698819 0.477652 0.057 Uiso 1 1 calc R U . . .
H15B H 0.358706 0.427801 0.515992 0.057 Uiso 1 1 calc R U . . .
H15C H 0.288448 0.775681 0.511581 0.057 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
C11 O2 C14 116.78(13) . . ?
N2 N1 C1 110.86(13) . . ?
N2 N1 C2 119.92(13) . . ?
C1 N1 C2 129.22(14) . . ?
N3 N2 N1 108.34(13) . . ?
N2 N3 N4 108.33(13) . . ?
N3 N4 C1 111.03(13) . . ?
N3 N4 C8 119.99(13) . . ?
C1 N4 C8 128.97(14) . . ?
O1 C1 N4 129.26(15) . . ?
O1 C1 N1 129.29(15) . . ?
N4 C1 N1 101.45(14) . . ?
C3 C2 C7 121.03(15) . . ?
C3 C2 N1 120.34(14) . . ?
C7 C2 N1 118.63(15) . . ?
C4 C3 C2 120.14(15) . . ?
C3 C4 C5 118.71(16) . . ?
C3 C4 C15 120.59(15) . . ?
C5 C4 C15 120.69(16) . . ?
C6 C5 C4 120.88(17) . . ?
C7 C6 C5 120.73(16) . . ?
C6 C7 C2 118.51(16) . . ?
C13 C8 C9 120.40(15) . . ?
C13 C8 N4 120.85(14) . . ?
C9 C8 N4 118.74(14) . . ?
C10 C9 C8 119.63(15) . . ?
C9 C10 C11 120.41(15) . . ?
O2 C11 C12 124.60(15) . . ?
O2 C11 C10 115.58(14) . . ?
C12 C11 C10 119.81(15) . . ?
C11 C12 C13 120.05(15) . . ?
C12 C13 C8 119.68(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 1.222(2) . ?
O2 C11 1.3718(19) . ?
O2 C14 1.428(2) . ?
N1 N2 1.3680(19) . ?
N1 C1 1.384(2) . ?
N1 C2 1.425(2) . ?
N2 N3 1.280(2) . ?
N3 N4 1.3670(19) . ?
N4 C1 1.381(2) . ?
N4 C8 1.428(2) . ?
C2 C3 1.391(2) . ?
C2 C7 1.392(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.391(2) . ?
C4 C15 1.506(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.385(2) . ?
C8 C13 1.389(2) . ?
C8 C9 1.390(2) . ?
C9 C10 1.380(2) . ?
C10 C11 1.393(2) . ?
C11 C12 1.387(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 -0.40(19) . . . . ?
C2 N1 N2 N3 178.74(14) . . . . ?
N1 N2 N3 N4 0.09(18) . . . . ?
N2 N3 N4 C1 0.24(19) . . . . ?
N2 N3 N4 C8 -178.70(14) . . . . ?
N3 N4 C1 O1 -179.53(17) . . . . ?
C8 N4 C1 O1 -0.7(3) . . . . ?
N3 N4 C1 N1 -0.45(17) . . . . ?
C8 N4 C1 N1 178.37(15) . . . . ?
N2 N1 C1 O1 179.58(17) . . . . ?
C2 N1 C1 O1 0.5(3) . . . . ?
N2 N1 C1 N4 0.51(18) . . . . ?
C2 N1 C1 N4 -178.53(15) . . . . ?
N2 N1 C2 C3 165.18(15) . . . . ?
C1 N1 C2 C3 -15.9(3) . . . . ?
N2 N1 C2 C7 -14.3(2) . . . . ?
C1 N1 C2 C7 164.69(17) . . . . ?
C7 C2 C3 C4 0.6(3) . . . . ?
N1 C2 C3 C4 -178.87(15) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 C15 178.88(17) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C15 C4 C5 C6 -179.12(17) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C2 0.4(3) . . . . ?
C3 C2 C7 C6 -0.6(3) . . . . ?
N1 C2 C7 C6 178.81(16) . . . . ?
N3 N4 C8 C13 -167.94(15) . . . . ?
C1 N4 C8 C13 13.3(3) . . . . ?
N3 N4 C8 C9 12.1(2) . . . . ?
C1 N4 C8 C9 -166.67(16) . . . . ?
C13 C8 C9 C10 0.5(3) . . . . ?
N4 C8 C9 C10 -179.52(16) . . . . ?
C8 C9 C10 C11 -0.9(3) . . . . ?
C14 O2 C11 C12 0.0(2) . . . . ?
C14 O2 C11 C10 179.65(16) . . . . ?
C9 C10 C11 O2 -178.68(16) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
O2 C11 C12 C13 178.95(16) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 C8 0.3(3) . . . . ?
C9 C8 C13 C12 -0.2(3) . . . . ?
N4 C8 C13 C12 179.82(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168342105
