#------------------------------------------------------------------------------
#$Date: 2023-12-12 14:54:19 +0200 (Tue, 12 Dec 2023) $
#$Revision: 288248 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/33/1563360.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_1563360
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                 94.7400
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   6.8159
_cell_length_b                   10.0882
_cell_length_c                   20.5143
_cell_volume                     1405.742
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.899
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_sigmaI/netI    0.03893
_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        25.47
_diffrn_reflns_theta_max         28.21
_diffrn_reflns_theta_min         1.99
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      0.397
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'calc w =1/[1.3*σ²(Fo²)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0340
_refine_ls_wR_factor_ref         0.0369
_reflns_number_gt                3147
_reflns_number_total             3147
_reflns_threshold_expression     >2.0sigma(I)
_cod_data_source_file            lq5037.cif
_cod_data_source_block           210K
_cod_original_sg_symbol_Hall     'P ?'
_cod_original_sg_symbol_H-M      'P ?'
_cod_database_code               1563360
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 0.20600(5) 0.11284(3) -0.007091(17) 0.02544(6) Uani 1 d . . . .
Cl Cl2 0.11732(5) 0.28113(3) 0.117193(16) 0.02557(6) Uani 1 d . . . .
O O1 0.13533(13) 0.56691(9) 0.09446(4) 0.02469(16) Uani 1 d . . . .
O O2 0.29004(14) 0.27801(9) -0.11823(4) 0.02832(18) Uani 1 d . . . .
N N1 0.29787(18) 0.81400(12) -0.00665(6) 0.0315(2) Uani 1 d . . . .
N N2 0.41777(18) 0.59850(12) -0.16769(6) 0.0311(2) Uani 1 d . . . .
C C1 0.18084(19) 0.50001(14) 0.04667(6) 0.0184(2) Uani 1 d . . . .
C C2 0.24722(18) 0.56004(13) -0.01152(6) 0.0176(2) Uani 1 d . . . .
C C3 0.28858(19) 0.48683(13) -0.06604(6) 0.0180(2) Uani 1 d . . . .
C C4 0.2637(2) 0.34362(13) -0.06874(7) 0.0192(2) Uani 1 d . . . .
C C5 0.21315(19) 0.28241(13) -0.00758(6) 0.0188(2) Uani 1 d . . . .
C C6 0.17471(19) 0.35477(13) 0.04595(6) 0.0189(2) Uani 1 d . . . .
C C7 0.27532(19) 0.70004(14) -0.00926(6) 0.0208(2) Uani 1 d . . . .
C C8 0.35898(19) 0.54926(14) -0.12195(7) 0.0217(2) Uani 1 d . . . .
N N3 0.31909(17) 0.95339(11) 0.18293(6) 0.0271(2) Uani 1 d . . . .
N N4 0.99182(19) 1.20333(13) 0.24852(6) 0.0377(2) Uani 1 d . . . .
C C9 0.3515(2) 0.99951(15) 0.24446(7) 0.0264(2) Uani 1 d . . . .
H H9 0.2369(14) 0.9805(19) 0.2768(5) 0.05417 Uani 1 d D U . .
C C10 0.5220(2) 1.06812(14) 0.26341(7) 0.0245(2) Uani 1 d . . . .
H H10 0.5518(11) 1.1025(13) 0.3133(2) 0.04694 Uani 1 d D U . .
C C11 0.6574(2) 1.08877(13) 0.21770(7) 0.0235(2) Uani 1 d . . . .
C C12 0.6208(2) 1.04218(15) 0.15428(7) 0.0295(3) Uani 1 d . . . .
H H12 0.7300(10) 1.0547(13) 0.1193(3) 0.05669 Uani 1 d D U . .
C C13 0.4496(2) 0.97302(15) 0.13815(7) 0.0307(3) Uani 1 d . . . .
H H13 0.412(3) 0.9360(16) 0.0892(3) 0.06023 Uani 1 calc D U . .
C C14 0.1395(3) 0.87628(17) 0.16393(9) 0.0441(3) Uani 1 d . . . .
H H14Aa 0.0605(9) 0.9221(6) 0.1222(2) 0.06820 Uani 0.49 calc D U . 1
H H14Ba 0.1796(10) 0.7767(3) 0.1516(3) 0.07358 Uani 0.49 calc D U . 1
H H14Ca 0.0474(7) 0.8738(7) 0.2041(2) 0.06920 Uani 0.49 calc D U . 1
H H14Ab 0.174(6) 0.795(4) 0.146(2) 0.07177 Uani 0.51 calc D U . 2
H H14Bb 0.060(6) 0.859(4) 0.206(2) 0.06972 Uani 0.51 calc D U . 2
H H14Cb 0.045(6) 0.933(4) 0.127(2) 0.06798 Uani 0.51 calc D U . 2
C C15 0.8398(2) 1.15505(15) 0.23560(7) 0.0285(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 122.61(11) . . . ?
O1 C1 C2 122.46(11) . . . ?
C6 C1 C2 114.92(11) . . . ?
C1 C2 C7 116.04(11) . . . ?
C1 C2 C3 122.76(11) . . . ?
C7 C2 C3 121.17(11) . . . ?
C4 C3 C8 116.98(11) . . . ?
C4 C3 C2 121.87(11) . . . ?
C8 C3 C2 121.14(11) . . . ?
O2 C4 C5 122.52(11) . . . ?
O2 C4 C3 122.54(11) . . . ?
C5 C4 C3 114.89(11) . . . ?
Cl1 C5 C6 121.57(9) . . . ?
Cl1 C5 C4 115.80(9) . . . ?
C6 C5 C4 122.63(11) . . . ?
Cl2 C6 C5 121.88(9) . . . ?
Cl2 C6 C1 115.66(9) . . . ?
C5 C6 C1 122.46(11) . . . ?
N1 C7 C2 179.201(9) . . . ?
N2 C8 C3 179.035(10) . . . ?
C13 N3 C9 121.53(11) . . . ?
C13 N3 C14 118.57(12) . . . ?
C9 N3 C14 119.88(12) . . . ?
N3 C9 C10 120.42(12) . . . ?
N3 C9 H9 116.3(7) . . . ?
C10 C9 H9 123.3(7) . . . ?
C9 C10 C11 118.51(12) . . . ?
C9 C10 H10 120.93(16) . . . ?
C11 C10 H10 120.53(16) . . . ?
C15 C11 C10 120.63(12) . . . ?
C15 C11 C12 118.92(12) . . . ?
C10 C11 C12 120.42(12) . . . ?
C13 C12 C11 118.73(12) . . . ?
C13 C12 H12 121.01(17) . . . ?
C11 C12 H12 120.13(17) . . . ?
N3 C13 C12 120.38(12) . . . ?
N3 C13 H13 117.7(9) . . . ?
C12 C13 H13 121.8(8) . . . ?
N3 C14 H14Ca 109.5(3) . . . ?
N3 C14 H14Aa 109.5(4) . . . ?
N3 C14 H14Ba 109.5(4) . . . ?
H14Ca C14 H14Aa 109.5(4) . . . ?
H14Ca C14 H14Ba 109.5(5) . . . ?
H14Aa C14 H14Ba 109.5(4) . . . ?
N4 C15 C11 176.52(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 1.7114(13) . ?
Cl2 C6 1.7134(13) . ?
O1 C1 1.2502(15) . ?
O2 C4 1.2374(15) . ?
N1 C7 1.1606(16) . ?
N2 C8 1.1618(16) . ?
C1 C6 1.4659(18) . ?
C1 C2 1.4443(18) . ?
C2 C7 1.4255(19) . ?
C2 C3 1.3884(17) . ?
C3 C4 1.4552(18) . ?
C3 C8 1.4260(18) . ?
C4 C5 1.4647(18) . ?
C5 C6 1.3619(18) . ?
N3 C13 1.3453(18) . ?
N3 C9 1.3463(17) . ?
N3 C14 1.475(2) . ?
N4 C15 1.1555(18) . ?
C9 C10 1.3806(19) . ?
C9 H9 1.083(2) . ?
C10 C11 1.3847(18) . ?
C10 H10 1.083(2) . ?
C11 C15 1.433(2) . ?
C11 C12 1.3863(19) . ?
C12 C13 1.376(2) . ?
C12 H12 1.082(2) . ?
C13 H13 1.083(2) . ?
C14 H14Ca 1.0770(14) . ?
C14 H14Aa 1.0770(14) . ?
C14 H14Ba 1.0770(14) . ?
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 1.083(2) 2.394(5) 3.4582(19) 167.2(4) 1
C14 H14Ba O1 1.0770(14) 2.426(3) 3.4301(19) 154.7(3) 1
C14 H14Ab O1 0.94(4) 2.54(4) 3.4301(19) 159.(1) 1
C13 H13 Cl1 1.083(2) 2.933(15) 3.5786(15) 118.5(8) 1_565
C12 H12 N1 1.082(2) 2.657(11) 3.4440(19) 129.1(6) 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 . . . . 0.14(14) ?
Cl1 C5 C6 C1 . . . . 179.73(16) ?
Cl1 C5 C4 O2 . . . . 3.52(16) ?
Cl1 C5 C4 C3 . . . . -174.03(15) ?
Cl2 C6 C5 C4 . . . . -179.60(16) ?
Cl2 C6 C1 O1 . . . . -4.35(16) ?
Cl2 C6 C1 C2 . . . . 174.48(15) ?
O1 C1 C6 C5 . . . . 176.04(18) ?
O1 C1 C2 C7 . . . . 5.49(17) ?
O1 C1 C2 C3 . . . . -176.70(18) ?
O2 C4 C5 C6 . . . . -176.73(19) ?
O2 C4 C3 C8 . . . . -4.29(18) ?
O2 C4 C3 C2 . . . . 176.11(18) ?
C1 C6 C5 C4 . . . . 0.00(19) ?
C1 C2 C3 C4 . . . . 1.31(19) ?
C1 C2 C3 C8 . . . . -178.28(19) ?
C2 C1 C6 C5 . . . . -5.1(2) ?
C2 C3 C4 C5 . . . . -6.35(18) ?
C3 C4 C5 C6 . . . . 5.7(2) ?
C3 C2 C1 C6 . . . . 4.47(18) ?
C4 C3 C2 C7 . . . . 179.01(19) ?
C5 C4 C3 C8 . . . . 173.26(19) ?
C6 C1 C2 C7 . . . . -173.34(18) ?
C7 C2 C3 C8 . . . . -0.57(19) ?
N3 C13 C12 C11 . . . . 1.21(19) ?
N3 C13 C12 H12 . . . . 177.(1) ?
N3 C9 C10 C11 . . . . 0.35(19) ?
N3 C9 C10 H10 . . . . -178.(1) ?
C9 N3 C13 C12 . . . . -0.4(2) ?
C9 N3 C13 H13 . . . . -178.(1) ?
C9 N3 C14 H14Ca . . . . 4.5(5) ?
C9 N3 C14 H14Aa . . . . 124.5(4) ?
C9 N3 C14 H14Ba . . . . -115.5(4) ?
C9 C10 C11 C15 . . . . -177.7(2) ?
C9 C10 C11 C12 . . . . 0.5(2) ?
H9 C9 N3 C13 . . . . 179.(2) ?
H9 C9 N3 C14 . . . . -3.(2) ?
H9 C9 C10 C11 . . . . -179.(2) ?
H9 C9 C10 H10 . . . . 3.(2) ?
C10 C9 N3 C13 . . . . -0.4(2) ?
C10 C9 N3 C14 . . . . 177.9(2) ?
C10 C11 C12 C13 . . . . -1.3(2) ?
C10 C11 C12 H12 . . . . -177.(1) ?
H10 C10 C11 C15 . . . . 0.(1) ?
H10 C10 C11 C12 . . . . 179.(1) ?
C11 C12 C13 H13 . . . . 179.(1) ?
C12 C13 N3 C14 . . . . -178.7(2) ?
H12 C12 C13 H13 . . . . -5.(2) ?
H12 C12 C11 C15 . . . . 1.(1) ?
C13 N3 C14 H14Ca . . . . -177.1(5) ?
C13 N3 C14 H14Aa . . . . -57.1(4) ?
C13 N3 C14 H14Ba . . . . 62.9(4) ?
C13 C12 C11 C15 . . . . 176.9(2) ?
H13 C13 N3 C14 . . . . 4.(2) ?
