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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/1/56/33/1563361.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_1563361
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                 94.7350
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   6.8491
_cell_length_b                   10.0960(2)
_cell_length_c                   20.5281(3)
_cell_volume                     1414.64(3)
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.901
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_sigmaI/netI    0.03925
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_theta_full        25.42
_diffrn_reflns_theta_max         28.15
_diffrn_reflns_theta_min         1.99
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.000
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0408
_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          0.0356
_refine_ls_wR_factor_ref         0.0378
_reflns_number_gt                3168
_reflns_number_total             3168
_reflns_threshold_expression     >2.0sigma(I)
_cod_data_source_file            lq5037.cif
_cod_data_source_block           240K
_cod_original_sg_symbol_Hall     'P ?'
_cod_original_sg_symbol_H-M      'P ?'
_cod_database_code               1563361
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 0.20536(6) 0.11306(3) -0.007128(18) 0.02951(6) Uani 1 d . . . .
Cl Cl2 0.11695(6) 0.28112(4) 0.117060(17) 0.02941(6) Uani 1 d . . . .
O O1 0.13547(14) 0.56682(10) 0.09448(4) 0.02827(17) Uani 1 d . . . .
O O2 0.29004(15) 0.27806(10) -0.11802(5) 0.03258(19) Uani 1 d . . . .
N N1 0.29839(19) 0.81374(13) -0.00659(6) 0.0361(2) Uani 1 d . . . .
N N2 0.41726(19) 0.59843(13) -0.16724(6) 0.0362(2) Uani 1 d . . . .
C C1 0.1806(2) 0.50005(14) 0.04671(7) 0.0211(2) Uani 1 d . . . .
C C2 0.24710(19) 0.55997(14) -0.01147(7) 0.0207(2) Uani 1 d . . . .
C C3 0.2884(2) 0.48647(14) -0.06586(7) 0.0207(2) Uani 1 d . . . .
C C4 0.2639(2) 0.34367(14) -0.06853(7) 0.0222(2) Uani 1 d . . . .
C C5 0.21273(19) 0.28251(13) -0.00751(7) 0.0204(2) Uani 1 d . . . .
C C6 0.1741(2) 0.35440(14) 0.04586(7) 0.0211(2) Uani 1 d . . . .
C C7 0.2750(2) 0.69990(15) -0.00920(6) 0.0242(2) Uani 1 d . . . .
C C8 0.3587(2) 0.54911(14) -0.12169(7) 0.0247(2) Uani 1 d . . . .
N N3 0.31984(18) 0.95328(12) 0.18292(6) 0.0309(2) Uani 1 d . . . .
N N4 0.9901(2) 1.20323(14) 0.24824(6) 0.0433(3) Uani 1 d . . . .
C C9 0.3518(2) 0.99941(16) 0.24428(7) 0.0301(3) Uani 1 d . . . .
H H9 0.2444(19) 0.9822(17) 0.279(11) 0.03612 Uani 1 d D U . .
C C10 0.5215(2) 1.06808(15) 0.26319(7) 0.0278(3) Uani 1 d . . . .
H H10 0.548(2) 1.1051(16) 0.313(11) 0.03339 Uani 1 d D U . .
C C11 0.6568(2) 1.08866(14) 0.21758(7) 0.0265(2) Uani 1 d . . . .
C C12 0.6207(2) 1.04176(17) 0.15439(7) 0.0342(3) Uani 1 d . . . .
H H12 0.724(2) 1.0590(18) 0.118(11) 0.04107 Uani 1 d D U . .
C C13 0.4494(3) 0.97270(16) 0.13816(7) 0.0344(3) Uani 1 d . . . .
H H13 0.420(3) 0.9336(17) 0.089(11) 0.04128 Uani 1 d D U . .
C C14 0.1406(3) 0.8763(2) 0.16403(10) 0.0505(4) Uani 1 d . . . .
H H14A 0.053(3) 0.870(2) 0.205(11) 0.07571 Uani 1 calc D U . .
H H14B 0.058(3) 0.925(2) 0.124(11) 0.07571 Uani 1 calc D U . .
H H14C 0.180(3) 0.778(11) 0.1494(11) 0.07571 Uani 1 calc D U . .
C C15 0.8384(2) 1.15455(16) 0.23542(7) 0.0329(3) 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
O1 C1 C6 122.63(11) . . . ?
O1 C1 C2 122.54(11) . . . ?
C6 C1 C2 114.83(11) . . . ?
C1 C2 C7 115.99(12) . . . ?
C1 C2 C3 122.65(11) . . . ?
C7 C2 C3 121.33(12) . . . ?
C4 C3 C8 117.08(12) . . . ?
C4 C3 C2 122.03(12) . . . ?
C8 C3 C2 120.89(11) . . . ?
O2 C4 C5 122.49(11) . . . ?
O2 C4 C3 122.56(11) . . . ?
C5 C4 C3 114.92(11) . . . ?
Cl1 C5 C6 121.51(10) . . . ?
Cl1 C5 C4 115.75(9) . . . ?
C6 C5 C4 122.74(11) . . . ?
Cl2 C6 C5 122.08(9) . . . ?
Cl2 C6 C1 115.51(9) . . . ?
C5 C6 C1 122.40(12) . . . ?
N1 C7 C2 179.217(8) . . . ?
N2 C8 C3 179.038(11) . . . ?
C13 N3 C9 121.67(12) . . . ?
C13 N3 C14 118.60(13) . . . ?
C9 N3 C14 119.71(13) . . . ?
N3 C9 C10 120.36(13) . . . ?
N3 C9 H9 120.(11) . . . ?
C10 C9 H9 120.(3) . . . ?
C9 C10 C11 118.64(13) . . . ?
C9 C10 H10 121.(3) . . . ?
C11 C10 H10 121.(9) . . . ?
C15 C11 C12 118.87(13) . . . ?
C15 C11 C10 120.80(12) . . . ?
C12 C11 C10 120.30(12) . . . ?
C13 C12 C11 118.75(13) . . . ?
C13 C12 H12 120.(2) . . . ?
C11 C12 H12 121.(11) . . . ?
N3 C13 C12 120.29(13) . . . ?
N3 C13 H13 120.(9) . . . ?
C12 C13 H13 120.(2) . . . ?
N3 C14 H14B 109.(3) . . . ?
N3 C14 H14C 109.(3) . . . ?
N3 C14 H14A 110.(3) . . . ?
H14B C14 H14C 109.(5) . . . ?
H14B C14 H14A 109.(14) . . . ?
H14C C14 H14A 109.(4) . . . ?
N4 C15 C11 176.68(4) . . . ?
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 1.7115(14) . ?
Cl2 C6 1.7121(14) . ?
O1 C1 1.2496(15) . ?
O2 C4 1.2381(15) . ?
N1 C7 1.1610(17) . ?
N2 C8 1.1597(17) . ?
C1 C6 1.4712(19) . ?
C1 C2 1.4456(18) . ?
C2 C7 1.426(2) . ?
C2 C3 1.3890(18) . ?
C3 C4 1.4519(19) . ?
C3 C8 1.4270(19) . ?
C4 C5 1.4649(18) . ?
C5 C6 1.3584(18) . ?
N3 C13 1.3432(19) . ?
N3 C9 1.3438(18) . ?
N3 C14 1.477(2) . ?
N4 C15 1.1599(18) . ?
C9 C10 1.382(2) . ?
C9 H9 1.08(17) . ?
C10 C11 1.3859(19) . ?
C10 H10 1.1(2) . ?
C11 C15 1.432(2) . ?
C11 C12 1.384(2) . ?
C12 C13 1.382(2) . ?
C12 H12 1.08(17) . ?
C13 H13 1.1(2) . ?
C14 H14B 1.08(17) . ?
C14 H14C 1.08(11) . ?
C14 H14A 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
C13 H13 N1 1.1(2) 2.40(19) 3.459(2) 166.(2) 1
C14 H14C O1 1.08(11) 2.42(10) 3.435(2) 156.3(9) 1
C13 H13 Cl1 1.1(2) 2.98(15) 3.5880(16) 116.(9) 1_565
C12 H12 N1 1.08(17) 2.6(2) 3.452(2) 133.(11) 3_675
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 . . . . 0.38(12) ?
Cl1 C5 C6 C1 . . . . 179.67(14) ?
Cl1 C5 C4 O2 . . . . 3.76(15) ?
Cl1 C5 C4 C3 . . . . -174.18(13) ?
Cl2 C6 C5 C4 . . . . -179.31(14) ?
Cl2 C6 C1 O1 . . . . -4.42(14) ?
Cl2 C6 C1 C2 . . . . 174.38(13) ?
O1 C1 C6 C5 . . . . 176.24(17) ?
O1 C1 C2 C7 . . . . 5.30(15) ?
O1 C1 C2 C3 . . . . -176.85(16) ?
O2 C4 C5 C6 . . . . -176.53(17) ?
O2 C4 C3 C8 . . . . -4.46(16) ?
O2 C4 C3 C2 . . . . 175.96(16) ?
C1 C6 C5 C4 . . . . -0.03(17) ?
C1 C2 C3 C4 . . . . 1.21(17) ?
C1 C2 C3 C8 . . . . -178.35(17) ?
C2 C1 C6 C5 . . . . -4.97(18) ?
C2 C3 C4 C5 . . . . -6.10(16) ?
C3 C4 C5 C6 . . . . 5.53(18) ?
C3 C2 C1 C6 . . . . 4.36(16) ?
C4 C3 C2 C7 . . . . 178.95(17) ?
C5 C4 C3 C8 . . . . 173.48(17) ?
C6 C1 C2 C7 . . . . -173.49(17) ?
C7 C2 C3 C8 . . . . -0.61(17) ?
N3 C13 C12 C11 . . . . 0.82(18) ?
N3 C13 C12 H12 . . . . -179.(4) ?
N3 C9 C10 C11 . . . . 0.30(18) ?
N3 C9 C10 H10 . . . . -180.(4) ?
C9 N3 C13 C12 . . . . -0.12(18) ?
C9 N3 C13 H13 . . . . 180.(4) ?
C9 N3 C14 H14B . . . . 122.(3) ?
C9 N3 C14 H14C . . . . -118.(6) ?
C9 N3 C14 H14A . . . . 2.(3) ?
C9 C10 C11 C15 . . . . -177.48(19) ?
C9 C10 C11 C12 . . . . 0.40(19) ?
H9 C9 N3 C13 . . . . 180.(5) ?
H9 C9 N3 C14 . . . . -2.(5) ?
H9 C9 C10 C11 . . . . 180.(5) ?
H9 C9 C10 H10 . . . . 0.(6) ?
C10 C9 N3 C13 . . . . -0.44(19) ?
C10 C9 N3 C14 . . . . 178.05(19) ?
C10 C11 C12 C13 . . . . -0.95(19) ?
C10 C11 C12 H12 . . . . 179.(4) ?
H10 C10 C11 C15 . . . . 3.(5) ?
H10 C10 C11 C12 . . . . -180.(5) ?
C11 C12 C13 H13 . . . . -179.(3) ?
C12 C13 N3 C14 . . . . -178.6(2) ?
H12 C12 C13 H13 . . . . 1.(6) ?
H12 C12 C11 C15 . . . . -3.(4) ?
C13 N3 C14 H14B . . . . -60.(3) ?
C13 N3 C14 H14C . . . . 60.(5) ?
C13 N3 C14 H14A . . . . -180.(4) ?
C13 C12 C11 C15 . . . . 177.0(2) ?
H13 C13 N3 C14 . . . . 1.(5) ?
