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#$Date: 2023-12-12 14:54:19 +0200 (Tue, 12 Dec 2023) $
#$Revision: 288248 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/33/1563370.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1563370
loop_
_publ_author_name
'Milašinović, Valentina'
'Molčanov, Krešimir'
'Krawczuk, Anna'
'Bogdanov, Nikita E.'
'Zakharov, Boris A.'
'Boldyreva, Elena V.'
'Jelsch, Christian'
'Kojić-Prodić, Biserka'
_publ_section_title
;
 Charge density studies of multicentre two-electron bonding of an anion
 radical at non-ambient temperature and pressure
;
_journal_issue                   4
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052252521005273
_journal_volume                  8
_journal_year                    2021
_chemical_formula_moiety         'C15 H7 Cl2 N4 O2'
_chemical_formula_sum            'C15 H7 Cl2 N4 O2'
_chemical_formula_weight         346.132
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'MoPro v20.01             '
_cell_angle_alpha                90.
_cell_angle_beta                 94.662(4)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   6.5155(3)
_cell_length_b                   9.94440(10)
_cell_length_c                   20.22930(10)
_cell_volume                     1306.38(6)
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_diffrn_measured_fraction_theta_full 0.581
_diffrn_measured_fraction_theta_max 0.520
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_sigmaI/netI    0.09749
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_theta_full        25.63
_diffrn_reflns_theta_max         27.91
_diffrn_reflns_theta_min         2.02
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.373
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         1632
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      13.885
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.1119
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0723
_reflns_number_gt                1632
_reflns_number_total             1632
_reflns_threshold_expression     >2.0sigma(I)
_cod_data_source_file            lq5037.cif
_cod_data_source_block           1.42GPa
_cod_original_sg_symbol_Hall     'P ?'
_cod_original_sg_symbol_H-M      'P ?'
_cod_database_code               1563370
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_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_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.21163(16) 0.10951(19) -0.00689(6) 0.0289(7) Uani 1 d . . . .
Cl Cl2 0.12324(16) 0.28000(19) 0.11910(5) 0.0287(7) Uani 1 d . . . .
O O1 0.1417(4) 0.5697(4) 0.09511(14) 0.0286(9) Uani 1 d . . . .
O O2 0.2992(4) 0.2737(5) -0.11935(14) 0.0327(9) Uani 1 d . . . .
N N1 0.2932(6) 0.8189(7) -0.00807(19) 0.0347(13) Uani 1 d . . . .
N N2 0.4158(5) 0.6012(6) -0.17224(18) 0.0301(10) Uani 1 d . . . .
N N3 0.3132(5) 0.9565(6) 0.18063(18) 0.0289(9) Uani 1 d . . . .
N N4 1.0089(5) 1.2130(6) 0.25161(18) 0.0376(10) Uani 1 d . . . .
C C1 0.1875(6) 0.5006(7) 0.0474(2) 0.0182(9) Uani 1 d . . . .
C C2 0.2501(6) 0.5590(8) -0.0129(2) 0.0242(10) Uani 1 d . . . .
C C3 0.2938(6) 0.4874(7) -0.0673(2) 0.0197(9) Uani 1 d . . . .
C C4 0.2725(7) 0.3432(8) -0.0698(2) 0.0231(10) Uani 1 d . . . .
C C5 0.2191(6) 0.2824(8) -0.0073(2) 0.022(2) Uiso 1 d . . . .
C C6 0.1812(6) 0.3525(7) 0.0465(2) 0.0191(10) Uani 1 d . . . .
C C7 0.2765(7) 0.7010(9) -0.0113(2) 0.0220(14) Uani 1 d . . . .
C C8 0.3597(6) 0.5506(7) -0.1247(2) 0.0248(10) Uani 1 d . . . .
C C9 0.3437(7) 1.0009(7) 0.2434(2) 0.0269(10) Uani 1 d . . . .
H H9 0.229(5) 0.982(7) 0.278(14) 0.03228 Uiso 1 d D U . .
C C10 0.5193(6) 1.0729(7) 0.2635(2) 0.0240(9) Uani 1 d . . . .
H H10 0.544(7) 1.109(6) 0.314(14) 0.02881 Uiso 1 d D U . .
C C11 0.6606(6) 1.0949(7) 0.2178(2) 0.0238(9) Uani 1 d . . . .
C C12 0.6294(7) 1.0510(7) 0.1537(2) 0.0310(11) Uani 1 d . . . .
H H12 0.741(5) 1.069(7) 0.118(14) 0.03716 Uiso 1 d D U . .
C C13 0.4507(7) 0.9787(7) 0.1362(2) 0.0287(10) Uani 1 d . . . .
H H13 0.422(7) 0.941(6) 0.086(14) 0.03448 Uiso 1 d D U . .
C C14 0.1303(9) 0.8756(11) 0.1597(3) 0.0468(11) Uani 1 d . . . .
H H14A 0.133(8) 0.849(8) 0.108(14) 0.07018 Uiso 1 calc D U . .
H H14B 0.131(10) 0.785(5) 0.189(14) 0.07018 Uiso 1 calc D U . .
H H14C -0.007(14) 0.933(6) 0.167(3) 0.07018 Uiso 1 calc D U . .
C C15 0.8512(7) 1.1619(7) 0.2380(2) 0.0291(10) Uani 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 0.0033 0.0016
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
H H 0.0000 0.0000
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
N N 0.0061 0.0033
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
O O 0.0106 0.0060
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
Cl Cl 0.1484 0.1585
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N3 C9 121.7(4) . . . ?
C13 N3 C14 117.9(4) . . . ?
C9 N3 C14 120.4(4) . . . ?
O1 C1 C6 123.7(5) . . . ?
O1 C1 C2 122.6(4) . . . ?
C6 C1 C2 113.7(5) . . . ?
C1 C2 C7 115.0(5) . . . ?
C1 C2 C3 124.5(4) . . . ?
C7 C2 C3 120.4(6) . . . ?
C4 C3 C8 116.5(5) . . . ?
C4 C3 C2 121.6(6) . . . ?
C8 C3 C2 121.9(4) . . . ?
O2 C4 C5 121.6(4) . . . ?
O2 C4 C3 124.3(5) . . . ?
C5 C4 C3 114.1(5) . . . ?
Cl1 C5 C6 120.8(5) . . . ?
Cl1 C5 C4 115.2(5) . . . ?
C6 C5 C4 124.1(4) . . . ?
Cl2 C6 C5 123.4(4) . . . ?
Cl2 C6 C1 114.8(4) . . . ?
C5 C6 C1 121.7(5) . . . ?
N1 C7 C2 177.50(10) . . . ?
N2 C8 C3 179.03(5) . . . ?
N3 C9 C10 120.2(4) . . . ?
N3 C9 H9 120.(14) . . . ?
C10 C9 H9 120.(4) . . . ?
C9 C10 C11 117.9(4) . . . ?
C9 C10 H10 120.(4) . . . ?
C11 C10 H10 122.(11) . . . ?
C15 C11 C12 118.4(4) . . . ?
C15 C11 C10 119.5(4) . . . ?
C12 C11 C10 122.0(4) . . . ?
C13 C12 C11 117.6(4) . . . ?
C13 C12 H12 121.(4) . . . ?
C11 C12 H12 122.(14) . . . ?
N3 C13 C12 120.5(4) . . . ?
N3 C13 H13 120.(11) . . . ?
C12 C13 H13 119.(4) . . . ?
N3 C14 H14C 110.(4) . . . ?
N3 C14 H14A 110.(5) . . . ?
N3 C14 H14B 109.(5) . . . ?
H14C C14 H14A 109.(6) . . . ?
H14C C14 H14B 110.(6) . . . ?
H14A C14 H14B 109.(17) . . . ?
N4 C15 C11 176.63(12) . . . ?
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
Cl1 C5 1.720(8) . ?
Cl2 C6 1.705(5) . ?
O1 C1 1.240(6) . ?
O2 C4 1.242(6) . ?
N1 C7 1.179(9) . ?
N2 C8 1.170(5) . ?
N3 C13 1.338(5) . ?
N3 C9 1.343(6) . ?
N3 C14 1.471(8) . ?
N4 C15 1.160(6) . ?
C1 C6 1.473(9) . ?
C1 C2 1.440(7) . ?
C2 C7 1.423(9) . ?
C2 C3 1.359(7) . ?
C3 C4 1.441(9) . ?
C3 C8 1.418(7) . ?
C4 C5 1.468(7) . ?
C5 C6 1.334(7) . ?
C9 C10 1.383(7) . ?
C9 H9 1.1(2) . ?
C10 C11 1.374(5) . ?
C10 H10 1.1(3) . ?
C11 C15 1.439(7) . ?
C11 C12 1.367(6) . ?
C12 C13 1.390(7) . ?
C12 H12 1.1(2) . ?
C13 H13 1.1(3) . ?
C14 H14C 1.08(9) . ?
C14 H14A 1.1(3) . ?
C14 H14B 1.08(16) . ?
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
C14 H14B C10 1.08(16) 2.55(12) 3.560(10) 156.(3) 2_545
C13 H13 N1 1.1(3) 2.4(2) 3.407(7) 163.(3) 1
C9 H9 Cl2 1.1(2) 2.99(19) 3.538(6) 111.(11) 2
C10 H10 O1 1.1(3) 2.3(2) 3.127(5) 130.(14) 2
C13 H13 Cl1 1.1(3) 2.79(18) 3.430(5) 117.(11) 1_565
C9 H9 N2 1.1(2) 2.49(14) 3.534(6) 162.(5) 4_576
C14 H14B N4 1.08(16) 2.64(12) 3.267(8) 116.(7) 2_645
C12 H12 Cl1 1.1(2) 2.9(2) 3.598(5) 122.(13) 3_665
C12 H12 N1 1.1(2) 2.5(3) 3.294(7) 131.(14) 3_675
C10 H10 O2 1.1(3) 2.36(15) 3.252(6) 138.(10) 4_676
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cl1 C5 C6 Cl2 . . . . 0.0(3) ?
Cl1 C5 C6 C1 . . . . 179.7(3) ?
Cl1 C5 C4 O2 . . . . 3.6(3) ?
Cl1 C5 C4 C3 . . . . -175.3(3) ?
Cl2 C6 C5 C4 . . . . -179.0(3) ?
Cl2 C6 C1 O1 . . . . -4.6(3) ?
Cl2 C6 C1 C2 . . . . 176.1(3) ?
O1 C1 C6 C5 . . . . 175.7(4) ?
O1 C1 C2 C7 . . . . 6.3(3) ?
O1 C1 C2 C3 . . . . -177.3(4) ?
O2 C4 C5 C6 . . . . -177.4(4) ?
O2 C4 C3 C8 . . . . -3.3(4) ?
O2 C4 C3 C2 . . . . 175.8(4) ?
N3 C13 C12 C11 . . . . 1.5(6) ?
N3 C13 C12 H12 . . . . -180.(5) ?
N3 C9 C10 C11 . . . . -1.1(6) ?
N3 C9 C10 H10 . . . . -180.(4) ?
C1 C6 C5 C4 . . . . 0.8(4) ?
C1 C2 C3 C4 . . . . 2.5(4) ?
C1 C2 C3 C8 . . . . -178.4(4) ?
C2 C1 C6 C5 . . . . -3.7(4) ?
C2 C3 C4 C5 . . . . -5.3(4) ?
C3 C4 C5 C6 . . . . 3.7(4) ?
C3 C2 C1 C6 . . . . 2.0(4) ?
C4 C3 C2 C7 . . . . 178.7(4) ?
C5 C4 C3 C8 . . . . 175.6(4) ?
C6 C1 C2 C7 . . . . -174.3(3) ?
C7 C2 C3 C8 . . . . -2.2(4) ?
C9 N3 C13 C12 . . . . -1.0(6) ?
C9 N3 C13 H13 . . . . 180.(4) ?
C9 N3 C14 H14C . . . . 60.(3) ?
C9 N3 C14 H14A . . . . -180.(4) ?
C9 N3 C14 H14B . . . . -60.(4) ?
C9 C10 C11 C15 . . . . -176.0(6) ?
C9 C10 C11 C12 . . . . 1.7(7) ?
H9 C9 N3 C13 . . . . 179.(6) ?
H9 C9 N3 C14 . . . . -4.(6) ?
H9 C9 C10 C11 . . . . -180.(6) ?
H9 C9 C10 H10 . . . . 1.(8) ?
C10 C9 N3 C13 . . . . 0.8(6) ?
C10 C9 N3 C14 . . . . 177.8(7) ?
C10 C11 C12 C13 . . . . -1.9(7) ?
C10 C11 C12 H12 . . . . 180.(5) ?
H10 C10 C11 C15 . . . . 3.(6) ?
H10 C10 C11 C12 . . . . -179.(6) ?
C11 C12 C13 H13 . . . . -179.(4) ?
C12 C13 N3 C14 . . . . -178.1(7) ?
H12 C12 C13 H13 . . . . -1.(7) ?
H12 C12 C11 C15 . . . . -3.(6) ?
C13 N3 C14 H14C . . . . -123.(3) ?
C13 N3 C14 H14A . . . . -3.(5) ?
C13 N3 C14 H14B . . . . 117.(4) ?
C13 C12 C11 C15 . . . . 175.8(6) ?
H13 C13 N3 C14 . . . . 3.(5) ?
