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#$Date: 2023-10-06 03:08:39 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286749 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/73/7247374.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_7247374
loop_
_publ_author_name
'Romanenko, Galina V.'
'Fokin, Sergey V.'
'Tolstikov, Svyatoslav E.'
'Letyagin, Gleb A.'
'Ovcharenko, Victor I.'
'Strizhenko, Kirill V.'
'Sheremetev, Aleksei B.'
_publ_section_title
;
 A co-crystal of heterobicyclic isomers as a product of the
 cyclocondensation reaction of 3,4-diaminofurazan with
 diethyl-2-oxosuccinate
;
_journal_issue                   38
_journal_name_full               CrystEngComm
_journal_page_first              5413
_journal_page_last               5419
_journal_paper_doi               10.1039/D3CE00769C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C8 H8 N4 O4'
_chemical_formula_weight         224.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-07-02 deposited with the CCDC.	2023-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                96.563(6)
_cell_angle_beta                 102.071(6)
_cell_angle_gamma                108.791(5)
_cell_formula_units_Z            2
_cell_length_a                   7.0461(7)
_cell_length_b                   7.5519(6)
_cell_length_c                   9.8725(9)
_cell_measurement_reflns_used    3105
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.64
_cell_measurement_theta_min      4.67
_cell_volume                     476.88(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5681
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.751
_diffrn_reflns_theta_min         4.671
_exptl_absorpt_coefficient_mu    1.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow_lemon
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0051(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         1696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0365
_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)+(0.0505P)²+0.1164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1520
_reflns_number_total             1696
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00769c2.cif
_cod_data_source_block           777a
_cod_depositor_comments
'Adding full bibliography for 7247374--7247376.cif.'
_cod_database_code               7247374
_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. 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 1.0429(2) 0.56110(18) 0.85622(14) 0.0629(4) Uani 1 1 d . . . . .
N2 N 0.9061(2) 0.3820(2) 0.78355(17) 0.0560(4) Uani 1 1 d . . . . .
C3 C 0.8232(2) 0.4064(2) 0.66013(17) 0.0395(4) Uani 1 1 d . . . . .
N4 N 0.6782(2) 0.25454(18) 0.56133(15) 0.0441(3) Uani 1 1 d . . . . .
H4A H 0.647(4) 0.144(4) 0.589(3) 0.077(7) Uiso 1 1 d . . . . .
C5 C 0.5767(2) 0.2522(2) 0.42682(17) 0.0400(4) Uani 1 1 d . . . . .
O6 O 0.4487(2) 0.10166(16) 0.35502(13) 0.0545(3) Uani 1 1 d . . . . .
C7 C 0.6106(2) 0.4236(2) 0.36428(18) 0.0407(4) Uani 1 1 d . . . . .
H7A H 0.527(3) 0.392(3) 0.268(2) 0.049(5) Uiso 1 1 d . . . . .
C8 C 0.7326(2) 0.6071(2) 0.41390(16) 0.0374(3) Uani 1 1 d . . . . .
C9 C 0.7292(2) 0.7521(2) 0.31992(17) 0.0424(4) Uani 1 1 d . . . . .
O10 O 0.8387(2) 0.91549(16) 0.36072(14) 0.0642(4) Uani 1 1 d . . . . .
O11 O 0.59427(19) 0.67951(16) 0.19626(13) 0.0541(3) Uani 1 1 d . . . . .
C12 C 0.5840(3) 0.8093(3) 0.0960(2) 0.0594(5) Uani 1 1 d . . . . .
H12A H 0.443(4) 0.752(3) 0.037(3) 0.073(6) Uiso 1 1 d . . . . .
H12B H 0.605(3) 0.940(4) 0.154(3) 0.072(6) Uiso 1 1 d . . . . .
C13 C 0.7420(4) 0.8206(4) 0.0168(3) 0.0744(6) Uani 1 1 d . . . . .
H13A H 0.719(4) 0.889(4) -0.058(3) 0.079(7) Uiso 1 1 d . . . . .
H13B H 0.885(4) 0.879(4) 0.088(3) 0.088(8) Uiso 1 1 d . . . . .
H13C H 0.744(5) 0.704(5) -0.028(3) 0.106(10) Uiso 1 1 d . . . . .
N14 N 0.8686(2) 0.69169(19) 0.54269(15) 0.0446(4) Uani 1 1 d . . . . .
H14A H 0.933(3) 0.810(3) 0.554(2) 0.060(6) Uiso 1 1 d . . . . .
C15 C 0.9076(2) 0.6027(2) 0.65354(16) 0.0378(3) Uani 1 1 d . . . . .
N16 N 1.0407(2) 0.6959(2) 0.77268(15) 0.0516(4) Uani 1 1 d . . . . .
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
N16 O1 N2 110.54(12) . . ?
C3 N2 O1 105.64(13) . . ?
N2 C3 N4 120.38(14) . . ?
N2 C3 C15 108.95(15) . . ?
N4 C3 C15 130.67(14) . . ?
C5 N4 C3 128.65(13) . . ?
O6 C5 N4 118.96(14) . . ?
O6 C5 C7 117.95(15) . . ?
N4 C5 C7 123.08(14) . . ?
C8 C7 C5 132.96(16) . . ?
C7 C8 N14 129.54(14) . . ?
C7 C8 C9 119.58(14) . . ?
N14 C8 C9 110.88(13) . . ?
O10 C9 O11 125.70(15) . . ?
O10 C9 C8 120.87(15) . . ?
O11 C9 C8 113.41(13) . . ?
C9 O11 C12 117.23(13) . . ?
C13 C12 O11 109.94(17) . . ?
C8 N14 C15 126.11(14) . . ?
N16 C15 N14 121.57(14) . . ?
N16 C15 C3 109.44(14) . . ?
N14 C15 C3 128.97(15) . . ?
C15 N16 O1 105.43(13) . . ?
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 N16 1.3832(18) . ?
O1 N2 1.3862(19) . ?
N2 C3 1.297(2) . ?
C3 N4 1.372(2) . ?
C3 C15 1.423(2) . ?
N4 C5 1.366(2) . ?
C5 O6 1.223(2) . ?
C5 C7 1.469(2) . ?
C7 C8 1.342(2) . ?
C8 N14 1.361(2) . ?
C8 C9 1.517(2) . ?
C9 O10 1.193(2) . ?
C9 O11 1.312(2) . ?
O11 C12 1.478(2) . ?
C12 C13 1.476(3) . ?
N14 C15 1.373(2) . ?
C15 N16 1.297(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4A O6 0.88(3) 1.94(3) 2.8257(17) 175(2) 2_656 yes
N14 H14A O10 0.84(2) 2.12(2) 2.9246(19) 160(2) 2_776 yes
