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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/1/56/33/1563368.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_1563368
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                 94.589(4)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   6.7445(3)
_cell_length_b                   10.04860(10)
_cell_length_c                   20.45390(10)
_cell_volume                     1381.77(6)
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_diffrn_measured_fraction_theta_full 0.581
_diffrn_measured_fraction_theta_max 0.504
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_sigmaI/netI    0.09766
_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       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_theta_full        25.95
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         2.00
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.804
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.000
_refine_ls_R_factor_all          0.1308
_refine_ls_R_factor_gt           0.1308
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                1716
_reflns_number_total             1716
_reflns_threshold_expression     >2.0sigma(I)
_cod_data_source_file            lq5037.cif
_cod_data_source_block           0.49GPa
_cod_original_sg_symbol_Hall     'P ?'
_cod_original_sg_symbol_H-M      'P ?'
_cod_database_code               1563368
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 0.20657(18) 0.1121(2) -0.00740(6) 0.03628 Uani 1 d . . . .
Cl Cl2 0.11952(18) 0.2805(2) 0.11755(6) 0.03485 Uani 1 d . . . .
O O1 0.1369(4) 0.5668(5) 0.09428(15) 0.03201 Uani 1 d . . . .
O O2 0.2914(5) 0.2764(5) -0.11883(16) 0.03561 Uani 1 d . . . .
N N1 0.2970(6) 0.8162(7) -0.0075(2) 0.04287 Uani 1 d . . . .
N N2 0.4184(5) 0.5990(6) -0.1685(2) 0.03860 Uani 1 d . . . .
N N3 0.3167(5) 0.9536(6) 0.1826(2) 0.03480 Uani 1 d . . . .
N N4 0.9948(6) 1.2075(7) 0.2490(2) 0.04994 Uani 1 d . . . .
C C1 0.1831(6) 0.4991(8) 0.0475(2) 0.02614 Uani 1 d . . . .
C C2 0.2475(6) 0.5593(8) -0.0117(2) 0.02527 Uani 1 d . . . .
C C3 0.2892(6) 0.4879(8) -0.0654(2) 0.02423 Uani 1 d . . . .
C C4 0.2681(7) 0.3437(8) -0.0683(3) 0.02953 Uani 1 d . . . .
C C5 0.2141(6) 0.2821(8) -0.0084(2) 0.02873 Uani 1 d . . . .
C C6 0.1757(6) 0.3522(8) 0.0461(2) 0.02451 Uani 1 d . . . .
C C7 0.2771(7) 0.6994(8) -0.0097(2) 0.02381 Uani 1 d . . . .
C C8 0.3593(6) 0.5476(7) -0.1221(2) 0.02552 Uani 1 d . . . .
C C9 0.3496(7) 1.0007(7) 0.2442(2) 0.02693 Uani 1 d . . . .
H H9 0.240(5) 0.983(7) 0.279(16) 0.03232 Uani 1 d D U . .
C C10 0.5210(7) 1.0705(8) 0.2626(2) 0.03425 Uani 1 d . . . .
H H10 0.546(7) 1.107(7) 0.312(16) 0.04110 Uani 1 d D U . .
C C11 0.6584(7) 1.0892(8) 0.2178(2) 0.03269 Uani 1 d . . . .
C C12 0.6220(7) 1.0455(8) 0.1542(3) 0.03901 Uani 1 d . . . .
H H12 0.729(6) 1.061(7) 0.118(16) 0.04682 Uani 1 d D U . .
C C13 0.4518(8) 0.9763(8) 0.1385(2) 0.03989 Uani 1 d . . . .
H H13 0.422(7) 0.939(6) 0.089(16) 0.04787 Uani 1 d D U . .
C C14 0.1342(10) 0.8721(12) 0.1619(4) 0.05967 Uani 1 d . . . .
H H14A 0.134(9) 0.845(9) 0.111(16) 0.08951 Uani 1 calc D U . .
H H14B 0.136(11) 0.783(5) 0.191(16) 0.08951 Uani 1 calc D U . .
H H14C 0.002(16) 0.929(7) 0.169(3) 0.08951 Uani 1 calc D U . .
C C15 0.8418(8) 1.1548(8) 0.2364(2) 0.03708 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
C9 N3 C13 119.7(4) . . . ?
C9 N3 C14 121.4(5) . . . ?
C13 N3 C14 118.8(5) . . . ?
O1 C1 C6 123.7(5) . . . ?
O1 C1 C2 121.9(4) . . . ?
C6 C1 C2 114.4(5) . . . ?
C1 C2 C7 116.1(5) . . . ?
C1 C2 C3 123.3(5) . . . ?
C7 C2 C3 120.5(6) . . . ?
C4 C3 C8 115.1(5) . . . ?
C4 C3 C2 122.1(6) . . . ?
C8 C3 C2 122.7(4) . . . ?
O2 C4 C5 121.6(5) . . . ?
O2 C4 C3 123.4(6) . . . ?
C5 C4 C3 114.9(5) . . . ?
Cl1 C5 C6 120.0(5) . . . ?
Cl1 C5 C4 116.6(5) . . . ?
C6 C5 C4 123.4(5) . . . ?
Cl2 C6 C5 123.7(4) . . . ?
Cl2 C6 C1 114.7(4) . . . ?
C5 C6 C1 121.6(6) . . . ?
N1 C7 C2 178.27(7) . . . ?
N2 C8 C3 178.88(6) . . . ?
N3 C9 C10 120.4(4) . . . ?
N3 C9 H9 119.(16) . . . ?
C10 C9 H9 120.(4) . . . ?
C9 C10 C11 119.1(4) . . . ?
C9 C10 H10 120.(4) . . . ?
C11 C10 H10 121.(13) . . . ?
C15 C11 C10 120.3(4) . . . ?
C15 C11 C12 119.1(5) . . . ?
C10 C11 C12 120.7(4) . . . ?
C13 C12 C11 118.1(5) . . . ?
C13 C12 H12 121.(4) . . . ?
C11 C12 H12 121.(16) . . . ?
N3 C13 C12 122.0(5) . . . ?
N3 C13 H13 119.(13) . . . ?
C12 C13 H13 119.(4) . . . ?
N3 C14 H14A 110.(5) . . . ?
N3 C14 H14C 110.(5) . . . ?
N3 C14 H14B 109.(5) . . . ?
H14A C14 H14C 109.(6) . . . ?
H14A C14 H14B 110.(20) . . . ?
H14C C14 H14B 109.(7) . . . ?
N4 C15 C11 177.04(11) . . . ?
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 1.709(8) . ?
Cl2 C6 1.698(5) . ?
O1 C1 1.234(6) . ?
O2 C4 1.255(6) . ?
N1 C7 1.181(9) . ?
N2 C8 1.178(6) . ?
N3 C9 1.347(6) . ?
N3 C13 1.352(6) . ?
N3 C14 1.511(9) . ?
N4 C15 1.170(6) . ?
C1 C6 1.477(9) . ?
C1 C2 1.451(7) . ?
C2 C7 1.422(9) . ?
C2 C3 1.360(8) . ?
C3 C4 1.457(9) . ?
C3 C8 1.420(7) . ?
C4 C5 1.445(7) . ?
C5 C6 1.362(8) . ?
C9 C10 1.378(7) . ?
C9 H9 1.1(2) . ?
C10 C11 1.368(6) . ?
C10 H10 1.1(3) . ?
C11 C15 1.426(7) . ?
C11 C12 1.375(7) . ?
C12 C13 1.358(8) . ?
C12 H12 1.1(2) . ?
C13 H13 1.1(3) . ?
C14 H14A 1.1(3) . ?
C14 H14C 1.08(10) . ?
C14 H14B 1.08(19) . ?
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(19) 2.60(14) 3.595(12) 154.(4) 2_545
C13 H13 N1 1.1(3) 2.4(3) 3.477(8) 165.(3) 1
C10 H10 O1 1.1(3) 2.4(3) 3.195(6) 130.(16) 2
C13 H13 Cl1 1.1(3) 2.9(2) 3.565(6) 118.(13) 1_565
C12 H12 N1 1.1(2) 2.6(3) 3.391(7) 132.(16) 3_675
C10 H10 O2 1.1(3) 2.39(18) 3.297(7) 140.(12) 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 . . . . 0.2(3) ?
Cl1 C5 C6 C1 . . . . 179.3(3) ?
Cl1 C5 C4 O2 . . . . 5.9(3) ?
Cl1 C5 C4 C3 . . . . -175.1(3) ?
Cl2 C6 C5 C4 . . . . -177.9(3) ?
Cl2 C6 C1 O1 . . . . -5.7(3) ?
Cl2 C6 C1 C2 . . . . 175.0(3) ?
O1 C1 C6 C5 . . . . 175.1(3) ?
O1 C1 C2 C7 . . . . 7.3(3) ?
O1 C1 C2 C3 . . . . -176.4(3) ?
O2 C4 C5 C6 . . . . -175.9(4) ?
O2 C4 C3 C8 . . . . -6.4(3) ?
O2 C4 C3 C2 . . . . 174.6(4) ?
N3 C9 C10 C11 . . . . -1.0(6) ?
N3 C9 C10 H10 . . . . -179.(4) ?
N3 C13 C12 C11 . . . . 2.1(6) ?
N3 C13 C12 H12 . . . . 179.(5) ?
C1 C6 C5 C4 . . . . 1.1(3) ?
C1 C2 C3 C4 . . . . 1.4(4) ?
C1 C2 C3 C8 . . . . -177.5(4) ?
C2 C1 C6 C5 . . . . -4.1(4) ?
C2 C3 C4 C5 . . . . -4.4(4) ?
C3 C4 C5 C6 . . . . 3.1(4) ?
C3 C2 C1 C6 . . . . 2.9(3) ?
C4 C3 C2 C7 . . . . 177.6(3) ?
C5 C4 C3 C8 . . . . 174.6(4) ?
C6 C1 C2 C7 . . . . -173.5(3) ?
C7 C2 C3 C8 . . . . -1.4(3) ?
C9 N3 C13 C12 . . . . 0.3(6) ?
C9 N3 C13 H13 . . . . -179.(4) ?
C9 N3 C14 H14A . . . . 179.(5) ?
C9 N3 C14 H14C . . . . 59.(3) ?
C9 N3 C14 H14B . . . . -61.(4) ?
C9 C10 C11 C15 . . . . -176.6(6) ?
C9 C10 C11 C12 . . . . 3.4(6) ?
H9 C9 N3 C13 . . . . 179.(6) ?
H9 C9 N3 C14 . . . . -2.(6) ?
H9 C9 C10 C11 . . . . 179.(6) ?
H9 C9 C10 H10 . . . . 1.(7) ?
C10 C9 N3 C13 . . . . -0.8(6) ?
C10 C9 N3 C14 . . . . 177.5(6) ?
C10 C11 C12 C13 . . . . -3.9(7) ?
C10 C11 C12 H12 . . . . 179.(5) ?
H10 C10 C11 C15 . . . . 2.(6) ?
H10 C10 C11 C12 . . . . -178.(6) ?
C11 C12 C13 H13 . . . . -179.(4) ?
C12 C13 N3 C14 . . . . -178.1(7) ?
H12 C12 C13 H13 . . . . -2.(7) ?
H12 C12 C11 C15 . . . . -1.(6) ?
C13 N3 C14 H14A . . . . -2.(5) ?
C13 N3 C14 H14C . . . . -123.(3) ?
C13 N3 C14 H14B . . . . 117.(4) ?
C13 C12 C11 C15 . . . . 176.1(6) ?
H13 C13 N3 C14 . . . . 2.(5) ?
