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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/1/56/33/1563364.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_1563364
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                 94.709(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   6.8752
_cell_length_b                   10.1004(2)
_cell_length_c                   20.5391(4)
_cell_volume                     1421.47(4)
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_diffrn_measured_fraction_theta_full 0.906
_diffrn_measured_fraction_theta_max 0.802
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_sigmaI/netI    0.04742
_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       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_theta_full        25.92
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         1.99
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.000
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0432
_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          0.0384
_refine_ls_wR_factor_ref         0.0427
_reflns_number_gt                2812
_reflns_number_total             2812
_reflns_threshold_expression     >2.0sigma(I)
_cod_data_source_file            lq5037.cif
_cod_data_source_block           310K
_cod_original_sg_symbol_Hall     'P ?'
_cod_original_sg_symbol_H-M      'P ?'
_cod_database_code               1563364
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 0.20411(6) 0.11365(4) -0.00714(2) 0.03948(7) Uani 1 d . . . .
N N4 0.9866(2) 1.20211(16) 0.24776(7) 0.0578(3) Uani 1 d . . . .
Cl Cl2 0.11633(6) 0.28129(4) 0.116826(19) 0.03928(7) Uani 1 d . . . .
C C15 0.8369(3) 1.15355(18) 0.23512(8) 0.0442(3) Uani 1 d . . . .
O O1 0.13630(16) 0.56639(10) 0.09452(5) 0.03713(19) Uani 1 d . . . .
O O2 0.28997(17) 0.27846(10) -0.11754(5) 0.0433(2) Uani 1 d . . . .
N N1 0.2990(2) 0.81236(14) -0.00661(7) 0.0471(3) Uani 1 d . . . .
N N2 0.4169(2) 0.59810(14) -0.16645(7) 0.0471(3) Uani 1 d . . . .
C C1 0.1807(2) 0.49984(15) 0.04685(7) 0.0281(2) Uani 1 d . . . .
C C2 0.2473(2) 0.55981(14) -0.01117(7) 0.0272(2) Uani 1 d . . . .
C C3 0.2886(2) 0.48655(14) -0.06548(7) 0.0271(2) Uani 1 d . . . .
C C4 0.2640(2) 0.34411(15) -0.06814(8) 0.0291(3) Uani 1 d . . . .
C C5 0.2122(2) 0.28284(14) -0.00737(7) 0.0276(4) Uiso 1 d . . . .
C C6 0.1737(2) 0.35438(14) 0.04605(7) 0.0275(2) Uani 1 d . . . .
C C7 0.2758(2) 0.69931(16) -0.00880(7) 0.0320(3) Uani 1 d . . . .
C C8 0.3584(2) 0.54888(15) -0.12101(8) 0.0319(3) Uani 1 d . . . .
N N3 0.3210(2) 0.95314(13) 0.18330(7) 0.0407(3) Uani 1 d . . . .
C C9 0.3532(3) 0.99930(17) 0.24424(8) 0.0404(3) Uani 1 d . . . .
H H9 0.246(2) 0.9824(19) 0.279(9) 0.04850 Uani 1 d D U . .
C C10 0.5218(3) 1.06787(16) 0.26303(8) 0.0367(3) Uani 1 d . . . .
H H10 0.548(3) 1.1049(18) 0.312(9) 0.04400 Uani 1 d D U . .
C C11 0.6556(2) 1.08800(15) 0.21746(8) 0.0358(3) Uani 1 d . . . .
C C12 0.6196(3) 1.04140(18) 0.15442(9) 0.0459(3) Uani 1 d . . . .
H H12 0.722(2) 1.058(2) 0.118(9) 0.05505 Uani 1 d D U . .
C C13 0.4493(3) 0.97188(18) 0.13858(8) 0.0456(4) Uani 1 d . . . .
H H13 0.420(3) 0.9327(18) 0.090(9) 0.05473 Uani 1 d D U . .
C C14 0.1427(4) 0.8762(2) 0.16434(12) 0.0673(4) Uani 1 d . . . .
H H14A 0.055(3) 0.870(3) 0.205(9) 0.10102 Uani 1 calc D U . .
H H14B 0.061(4) 0.925(2) 0.124(9) 0.10102 Uani 1 calc D U . .
H H14C 0.182(4) 0.778(9) 0.1497(13) 0.10102 Uani 1 calc D U . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
N4 C15 C11 176.98(4) . . . ?
O1 C1 C6 122.54(12) . . . ?
O1 C1 C2 122.46(12) . . . ?
C6 C1 C2 114.98(12) . . . ?
C1 C2 C7 116.06(12) . . . ?
C1 C2 C3 122.64(12) . . . ?
C7 C2 C3 121.26(12) . . . ?
C4 C3 C8 117.12(12) . . . ?
C4 C3 C2 121.93(12) . . . ?
C8 C3 C2 120.95(12) . . . ?
O2 C4 C5 122.32(12) . . . ?
O2 C4 C3 122.59(12) . . . ?
C5 C4 C3 115.06(12) . . . ?
Cl1 C5 C6 121.41(10) . . . ?
Cl1 C5 C4 115.81(10) . . . ?
C6 C5 C4 122.78(12) . . . ?
Cl2 C6 C5 122.18(10) . . . ?
Cl2 C6 C1 115.65(10) . . . ?
C5 C6 C1 122.17(12) . . . ?
N1 C7 C2 179.724(3) . . . ?
N2 C8 C3 179.010(12) . . . ?
C9 N3 C13 121.67(13) . . . ?
C9 N3 C14 120.05(15) . . . ?
C13 N3 C14 118.25(16) . . . ?
N3 C9 C10 120.57(14) . . . ?
N3 C9 H9 120.(9) . . . ?
C10 C9 H9 120.(2) . . . ?
C9 C10 C11 118.45(14) . . . ?
C9 C10 H10 121.(2) . . . ?
C11 C10 H10 121.(7) . . . ?
C15 C11 C10 120.75(14) . . . ?
C15 C11 C12 118.75(15) . . . ?
C10 C11 C12 120.46(14) . . . ?
C13 C12 C11 118.54(15) . . . ?
C13 C12 H12 120.(2) . . . ?
C11 C12 H12 121.(9) . . . ?
N3 C13 C12 120.28(15) . . . ?
N3 C13 H13 120.(7) . . . ?
C12 C13 H13 120.(2) . . . ?
N3 C14 H14C 110.(3) . . . ?
N3 C14 H14B 109.(2) . . . ?
N3 C14 H14A 109.(2) . . . ?
H14C C14 H14B 109.(4) . . . ?
H14C C14 H14A 109.(4) . . . ?
H14B C14 H14A 109.(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 1.7098(15) . ?
N4 C15 1.151(2) . ?
Cl2 C6 1.7052(14) . ?
C15 C11 1.431(2) . ?
O1 C1 1.2460(16) . ?
O2 C4 1.2373(17) . ?
N1 C7 1.1533(19) . ?
N2 C8 1.1583(18) . ?
C1 C6 1.470(2) . ?
C1 C2 1.444(2) . ?
C2 C7 1.423(2) . ?
C2 C3 1.3871(19) . ?
C3 C4 1.449(2) . ?
C3 C8 1.421(2) . ?
C4 C5 1.463(2) . ?
C5 C6 1.3578(19) . ?
N3 C9 1.337(2) . ?
N3 C13 1.338(2) . ?
N3 C14 1.476(3) . ?
C9 C10 1.378(2) . ?
C9 H9 1.08(13) . ?
C10 C11 1.380(2) . ?
C10 H10 1.08(17) . ?
C11 C12 1.381(2) . ?
C12 C13 1.381(3) . ?
C12 H12 1.08(14) . ?
C13 H13 1.08(17) . ?
C14 H14C 1.08(8) . ?
C14 H14B 1.08(13) . ?
C14 H14A 1.08(15) . ?
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 1.08(17) 2.41(15) 3.471(2) 166.(2) 1
C14 H14C O1 1.08(8) 2.43(8) 3.441(3) 156.1(10) 1
C10 H10 O1 1.08(17) 2.41(15) 3.2037(19) 129.(9) 2
C12 H12 N1 1.08(14) 2.63(16) 3.463(2) 133.(9) 3_675
C10 H10 O2 1.08(17) 2.41(10) 3.329(2) 141.(7) 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 . . . . 0.40(17) ?
Cl1 C5 C6 C1 . . . . 179.73(19) ?
Cl1 C5 C4 O2 . . . . 3.8(2) ?
Cl1 C5 C4 C3 . . . . -174.30(19) ?
Cl2 C6 C5 C4 . . . . -179.2(2) ?
Cl2 C6 C1 O1 . . . . -4.2(2) ?
Cl2 C6 C1 C2 . . . . 174.42(19) ?
C15 C11 C10 C9 . . . . -177.3(3) ?
C15 C11 C10 H10 . . . . 3.(3) ?
C15 C11 C12 C13 . . . . 176.5(3) ?
C15 C11 C12 H12 . . . . -3.(4) ?
O1 C1 C6 C5 . . . . 176.4(2) ?
O1 C1 C2 C7 . . . . 5.3(2) ?
O1 C1 C2 C3 . . . . -177.1(2) ?
O2 C4 C5 C6 . . . . -176.6(2) ?
O2 C4 C3 C8 . . . . -4.4(2) ?
O2 C4 C3 C2 . . . . 175.9(2) ?
C1 C6 C5 C4 . . . . 0.1(2) ?
C1 C2 C3 C4 . . . . 1.2(2) ?
C1 C2 C3 C8 . . . . -178.4(2) ?
C2 C1 C6 C5 . . . . -5.0(3) ?
C2 C3 C4 C5 . . . . -6.0(2) ?
C3 C4 C5 C6 . . . . 5.3(3) ?
C3 C2 C1 C6 . . . . 4.3(2) ?
C4 C3 C2 C7 . . . . 178.7(2) ?
C5 C4 C3 C8 . . . . 173.7(2) ?
C6 C1 C2 C7 . . . . -173.4(2) ?
C7 C2 C3 C8 . . . . -0.9(2) ?
N3 C9 C10 C11 . . . . 0.2(2) ?
N3 C9 C10 H10 . . . . -180.(4) ?
N3 C13 C12 C11 . . . . 1.5(3) ?
N3 C13 C12 H12 . . . . -179.(4) ?
C9 N3 C13 C12 . . . . -0.6(3) ?
C9 N3 C13 H13 . . . . 180.(4) ?
C9 N3 C14 H14C . . . . -118.(6) ?
C9 N3 C14 H14B . . . . 122.(3) ?
C9 N3 C14 H14A . . . . 2.(4) ?
C9 C10 C11 C12 . . . . 0.7(3) ?
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 . . . . -0.2(3) ?
C10 C9 N3 C14 . . . . 178.1(3) ?
C10 C11 C12 C13 . . . . -1.5(3) ?
C10 C11 C12 H12 . . . . 179.(4) ?
H10 C10 C11 C12 . . . . -179.(5) ?
C11 C12 C13 H13 . . . . -179.(3) ?
C12 C13 N3 C14 . . . . -179.0(3) ?
H12 C12 C13 H13 . . . . 1.(6) ?
C13 N3 C14 H14C . . . . 60.(6) ?
C13 N3 C14 H14B . . . . -60.(4) ?
C13 N3 C14 H14A . . . . 180.(4) ?
H13 C13 N3 C14 . . . . 1.(5) ?
