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#$Date: 2025-04-05 06:55:56 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299060 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/03/7160351.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_7160351
loop_
_publ_author_name
'Tu, Shunqi'
'Chen, Tiantian'
'Yuan, Zijian'
'Wang, Jianchun'
_publ_section_title
;
 A new tetrazine catalytic system for the synthesis of
 N-aryl-α-arylated glycine ester derivatives.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2450
_journal_page_last               2455
_journal_paper_doi               10.1039/d4ob01993h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_sum            'C6 H3 N4 O3'
_chemical_formula_weight         179.12
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-11-20 deposited with the CCDC.	2025-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.380(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1663(2)
_cell_length_b                   10.7506(2)
_cell_length_c                   7.6582(2)
_cell_measurement_temperature    293(2)
_cell_volume                     720.21(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4242
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.410
_diffrn_reflns_theta_min         5.056
_exptl_absorpt_coefficient_mu    1.192
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0746
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1299P)²+0.1553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2048
_refine_ls_wR_factor_ref         0.2122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1228
_reflns_number_total             1441
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01993h2.cif
_cod_data_source_block           tsq-dj-02
_cod_depositor_comments          'Adding full bibliography for 7160351.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160351
_shelx_shelxl_version_number     2018/3
_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   0.755
_shelx_estimated_absorpt_t_max   0.842
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 0.54234(17) 0.54975(15) 0.3430(2) 0.0465(5) Uani 1 1 d . . . . .
N4 N 0.3589(2) 0.46095(17) -0.1007(2) 0.0428(5) Uani 1 1 d . . . . .
N3 N 0.3839(2) 0.4849(2) 0.0755(2) 0.0456(5) Uani 1 1 d . . . . .
O2 O 0.5795(3) 0.3081(2) 0.3830(3) 0.0817(8) Uani 1 1 d . . . . .
N2 N 0.6935(2) 0.32066(19) 0.5101(3) 0.0555(6) Uani 1 1 d . . . . .
N1 N 0.8971(2) 0.4463(2) 0.6774(3) 0.0552(6) Uani 1 1 d . . . . .
C6 C 0.5239(2) 0.52290(19) 0.1662(3) 0.0378(5) Uani 1 1 d . . . . .
C2 C 0.6902(2) 0.5514(2) 0.4632(3) 0.0406(6) Uani 1 1 d . . . . .
C1 C 0.7627(3) 0.44581(19) 0.5504(3) 0.0430(6) Uani 1 1 d . . . . .
O3 O 0.7483(3) 0.2391(2) 0.6142(5) 0.1187(12) Uani 1 1 d . . . . .
C3 C 0.7620(3) 0.6636(2) 0.5115(3) 0.0528(6) Uani 1 1 d . . . . .
H3 H 0.716848 0.736796 0.456091 0.063 Uiso 1 1 calc R U . . .
C5 C 0.9648(3) 0.5557(3) 0.7234(4) 0.0625(8) Uani 1 1 d . . . . .
H5 H 1.058779 0.557866 0.813778 0.075 Uiso 1 1 calc R U . . .
C4 C 0.9030(3) 0.6662(3) 0.6442(4) 0.0618(7) Uani 1 1 d . . . . .
H4 H 0.954710 0.740849 0.678940 0.074 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'
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
C6 O1 C2 118.22(17) . . ?
N3 N4 C6 116.52(17) . 3_665 ?
N4 N3 C6 115.99(18) . . ?
O3 N2 O2 123.3(2) . . ?
O3 N2 C1 117.5(2) . . ?
O2 N2 C1 119.0(2) . . ?
C1 N1 C5 117.2(2) . . ?
N4 C6 N3 127.49(19) 3_665 . ?
N4 C6 O1 118.71(18) 3_665 . ?
N3 C6 O1 113.78(19) . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 O1 118.91(19) . . ?
C1 C2 O1 122.79(19) . . ?
N1 C1 C2 124.1(2) . . ?
N1 C1 N2 113.83(18) . . ?
C2 C1 N2 122.1(2) . . ?
C2 C3 C4 118.9(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
N1 C5 C4 123.3(2) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.3 . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
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 C6 1.345(2) . ?
O1 C2 1.392(2) . ?
N4 N3 1.325(2) . ?
N4 C6 1.326(3) 3_665 ?
N3 C6 1.328(3) . ?
O2 N2 1.204(3) . ?
N2 O3 1.190(3) . ?
N2 C1 1.480(3) . ?
N1 C1 1.322(3) . ?
N1 C5 1.328(3) . ?
C2 C3 1.372(3) . ?
C2 C1 1.382(3) . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C5 C4 1.376(4) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
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
C6 N4 N3 C6 0.2(3) 3_665 . . . ?
N4 N3 C6 N4 -0.3(4) . . . 3_665 ?
N4 N3 C6 O1 178.03(16) . . . . ?
C2 O1 C6 N4 -21.8(3) . . . 3_665 ?
C2 O1 C6 N3 159.76(19) . . . . ?
C6 O1 C2 C3 100.3(2) . . . . ?
C6 O1 C2 C1 -86.3(3) . . . . ?
C5 N1 C1 C2 0.4(4) . . . . ?
C5 N1 C1 N2 -178.7(2) . . . . ?
C3 C2 C1 N1 -0.1(4) . . . . ?
O1 C2 C1 N1 -173.6(2) . . . . ?
C3 C2 C1 N2 179.0(2) . . . . ?
O1 C2 C1 N2 5.4(4) . . . . ?
O3 N2 C1 N1 13.2(4) . . . . ?
O2 N2 C1 N1 -171.9(2) . . . . ?
O3 N2 C1 C2 -165.9(3) . . . . ?
O2 N2 C1 C2 8.9(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
O1 C2 C3 C4 173.9(2) . . . . ?
C1 N1 C5 C4 -0.9(5) . . . . ?
N1 C5 C4 C3 0.9(5) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
