#------------------------------------------------------------------------------
#$Date: 2023-05-06 13:47:32 +0300 (Sat, 06 May 2023) $
#$Revision: 283590 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022728.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_2022728
loop_
_publ_author_name
'Vassilyeva, Olga Yu'
'Buvaylo, Elena A.'
'Kokozay, Vladimir N.'
'Skelton, Brian W.'
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld surface analysis of the hybrid
 salt bis-(2-methyl-imidazo[1,5-a]pyridin-2-ium)
 tetra-chlorido-manganate(II).
;
_journal_coeditor_code           JQ2027
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              397
_journal_page_last               401
_journal_paper_doi               10.1107/S2056989023002761
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          '(C8 H9 N2)2 [Mn Cl4]'
_chemical_formula_moiety         '2(C8 H9 N2 +), Cl4 Mn 2-'
_chemical_formula_sum            'C16 H18 Cl4 Mn N4'
_chemical_formula_weight         463.08
_chemical_name_systematic
;
Bis(2-methylimidazo[1,5-a]pyridin-2-ium) tetrachloridomanganate(II)
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                99.211(5)
_cell_angle_beta                 110.852(6)
_cell_angle_gamma                91.515(5)
_cell_formula_units_Z            2
_cell_length_a                   9.4042(6)
_cell_length_b                   10.7074(6)
_cell_length_c                   10.7401(6)
_cell_measurement_reflns_used    3962
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.18
_cell_measurement_theta_min      2.077
_cell_volume                     993.52(11)
_computing_cell_refinement
;
CrysAlis Pro (Rigaku OD, 2016)
;
_computing_data_collection
;
CrysAlis Pro (Rigaku OD, 2016)
;
_computing_data_reduction
;
CrysAlis Pro (Rigaku OD, 2016)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0009
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11038
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.11
_diffrn_reflns_theta_min         2.063
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.209
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlis Pro; Rigaku OD, 2016)
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       needle
_exptl_crystal_F_000             470
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.32
_refine_diff_density_min         -0.648
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         6374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0564P)²+0.8647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1263
_reflns_number_gt                5151
_reflns_number_total             6374
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jq2027sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022728.cif.'
_cod_database_code               2022728
_cod_database_fobs_code          2022728
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C11 0.7645(3) 0.5468(2) 0.2669(2) 0.0213(4) Uani d 1 . .
H H11 0.838597 0.50728 0.330658 0.026 Uiso calc 1 . .
N N12 0.7899(2) 0.61515(18) 0.18183(18) 0.0182(3) Uani d 1 . .
C C12 0.9382(3) 0.6391(2) 0.1700(3) 0.0256(5) Uani d 1 . .
H H12A 0.989164 0.719825 0.228348 0.038 Uiso calc 1 . .
H H12B 0.922869 0.643492 0.075695 0.038 Uiso calc 1 . .
H H12C 1.001665 0.570072 0.198003 0.038 Uiso calc 1 . .
C C13 0.6572(2) 0.6572(2) 0.1041(2) 0.0204(4) Uani d 1 . .
H H13 0.645655 0.70732 0.036315 0.024 Uiso calc 1 . .
N N13A 0.5446(2) 0.6135(2) 0.1425(2) 0.0266(4) Uani d 1 . .
C C14 0.3856(3) 0.6248(2) 0.1000(3) 0.0253(5) Uani d 1 . .
H H14 0.336093 0.668856 0.02843 0.03 Uiso calc 1 . .
C C15 0.3062(3) 0.5714(3) 0.1637(3) 0.0315(6) Uani d 1 . .
H H15 0.199452 0.578985 0.136942 0.038 Uiso calc 1 . .
C C16 0.3786(3) 0.5039(3) 0.2702(3) 0.0352(6) Uani d 1 . .
H H16 0.319686 0.468677 0.314078 0.042 Uiso calc 1 . .
C C17 0.5293(3) 0.4893(2) 0.3098(3) 0.0303(5) Uani d 1 . .
H H17 0.576756 0.442786 0.37962 0.036 Uiso calc 1 . .
C C17A 0.6142(2) 0.54440(19) 0.2455(2) 0.0153(4) Uani d 1 . .
C C21 0.2932(3) 0.8976(2) 0.3195(2) 0.0250(5) Uani d 1 . .
H H21 0.196989 0.897717 0.329702 0.03 Uiso calc 1 . .
N N22 0.3271(3) 0.9359(2) 0.2170(2) 0.0267(4) Uani d 1 . .
C C22 0.2201(4) 0.9879(3) 0.1047(3) 0.0370(6) Uani d 1 . .
H H22A 0.275187 1.01841 0.051736 0.056 Uiso calc 1 . .
H H22B 0.173674 1.058598 0.14116 0.056 Uiso calc 1 . .
H H22C 0.139884 0.921389 0.046435 0.056 Uiso calc 1 . .
C C23 0.4729(3) 0.9225(2) 0.2345(2) 0.0260(5) Uani d 1 . .
H H23 0.523166 0.942318 0.176507 0.031 Uiso calc 1 . .
N N23A 0.5364(2) 0.87586(19) 0.3492(2) 0.0232(4) Uani d 1 . .
C C24 0.6858(3) 0.8453(2) 0.4119(3) 0.0289(5) Uani d 1 . .
H H24 0.761335 0.85674 0.374017 0.035 Uiso calc 1 . .
C C25 0.7194(3) 0.7991(3) 0.5275(3) 0.0337(6) Uani d 1 . .
H H25 0.819593 0.775808 0.570203 0.04 Uiso calc 1 . .
C C26 0.6093(3) 0.7844(2) 0.5870(3) 0.0334(6) Uani d 1 . .
H H26 0.63787 0.75435 0.670355 0.04 Uiso calc 1 . .
C C27 0.4650(3) 0.8124(2) 0.5276(3) 0.0281(5) Uani d 1 . .
H H27 0.391259 0.800913 0.567407 0.034 Uiso calc 1 . .
C C27A 0.4246(3) 0.8592(2) 0.4045(2) 0.0202(4) Uani d 1 . .
Mn Mn1 0.84578(4) 0.19104(3) 0.25082(3) 0.02042(9) Uani d 1 . .
Cl Cl1 0.57864(6) 0.18756(6) 0.13323(6) 0.02657(13) Uani d 1 . .
Cl Cl2 0.98756(7) 0.30020(6) 0.15037(6) 0.02681(13) Uani d 1 . .
Cl Cl3 0.90155(8) -0.02287(6) 0.24168(7) 0.03208(14) Uani d 1 . .
Cl Cl4 0.89538(7) 0.30780(6) 0.47087(6) 0.03045(14) Uani d 1 . .
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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0672
2 1 -1 0.0172
0 -1 1 0.0832
0 1 -1 0.0637
0 2 1 0.1701
0 -2 -1 0.1887
-2 -1 1 0.0812
-1 -3 3 0.0782
1 -1 1 0.064
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N12 C11 C17A . . 107.34(19) ?
N12 C11 H11 . . 126.3 ?
C17A C11 H11 . . 126.3 ?
C11 N12 C13 . . 110.61(19) ?
C11 N12 C12 . . 125.11(19) ?
C13 N12 C12 . . 124.3(2) ?
N12 C12 H12A . . 109.5 ?
N12 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N12 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N13A C13 N12 . . 106.9(2) ?
N13A C13 H13 . . 126.5 ?
N12 C13 H13 . . 126.5 ?
C13 N13A C17A . . 106.65(18) ?
C13 N13A C14 . . 133.6(2) ?
C17A N13A C14 . . 119.8(2) ?
C15 C14 N13A . . 118.2(2) ?
C15 C14 H14 . . 120.9 ?
N13A C14 H14 . . 120.9 ?
C14 C15 C16 . . 121.5(2) ?
C14 C15 H15 . . 119.2 ?
C16 C15 H15 . . 119.2 ?
C17 C16 C15 . . 121.1(2) ?
C17 C16 H16 . . 119.5 ?
C15 C16 H16 . . 119.5 ?
C16 C17 C17A . . 118.4(2) ?
C16 C17 H17 . . 120.8 ?
C17A C17 H17 . . 120.8 ?
C11 C17A C17 . . 130.5(2) ?
C11 C17A N13A . . 108.49(19) ?
C17 C17A N13A . . 121.0(2) ?
N22 C21 C27A . . 106.9(2) ?
N22 C21 H21 . . 126.5 ?
C27A C21 H21 . . 126.5 ?
C23 N22 C21 . . 110.4(2) ?
C23 N22 C22 . . 124.2(2) ?
C21 N22 C22 . . 125.3(2) ?
N22 C22 H22A . . 109.5 ?
N22 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
N22 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
N22 C23 N23A . . 107.7(2) ?
N22 C23 H23 . . 126.2 ?
N23A C23 H23 . . 126.2 ?
C23 N23A C24 . . 130.2(2) ?
C23 N23A C27A . . 108.6(2) ?
C24 N23A C27A . . 121.2(2) ?
C25 C24 N23A . . 118.0(2) ?
C25 C24 H24 . . 121 ?
N23A C24 H24 . . 121 ?
C24 C25 C26 . . 121.7(2) ?
C24 C25 H25 . . 119.1 ?
C26 C25 H25 . . 119.1 ?
C27 C26 C25 . . 121.0(2) ?
C27 C26 H26 . . 119.5 ?
C25 C26 H26 . . 119.5 ?
C26 C27 C27A . . 118.9(2) ?
C26 C27 H27 . . 120.5 ?
C27A C27 H27 . . 120.5 ?
C21 C27A N23A . . 106.4(2) ?
C21 C27A C27 . . 134.5(2) ?
N23A C27A C27 . . 119.0(2) ?
Cl3 Mn1 Cl4 . . 115.23(3) y
Cl3 Mn1 Cl1 . . 106.36(3) y
Cl4 Mn1 Cl1 . . 105.81(3) y
Cl3 Mn1 Cl2 . . 110.21(3) y
Cl4 Mn1 Cl2 . . 107.51(3) y
Cl1 Mn1 Cl2 . . 111.72(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C11 N12 . 1.337(3) ?
C11 C17A . 1.347(3) ?
C11 H11 . 0.95 ?
N12 C13 . 1.366(3) ?
N12 C12 . 1.464(3) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 N13A . 1.363(3) ?
C13 H13 . 0.95 ?
N13A C17A . 1.405(3) ?
N13A C14 . 1.414(3) ?
C14 C15 . 1.350(4) ?
C14 H14 . 0.95 ?
C15 C16 . 1.425(4) ?
C15 H15 . 0.95 ?
C16 C17 . 1.349(4) ?
C16 H16 . 0.95 ?
C17 C17A . 1.400(3) ?
C17 H17 . 0.95 ?
C21 N22 . 1.366(3) ?
C21 C27A . 1.369(3) ?
C21 H21 . 0.95 ?
N22 C23 . 1.332(3) ?
N22 C22 . 1.468(3) ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C23 N23A . 1.346(3) ?
C23 H23 . 0.95 ?
N23A C24 . 1.399(3) ?
N23A C27A . 1.400(3) ?
C24 C25 . 1.346(4) ?
C24 H24 . 0.95 ?
C25 C26 . 1.414(4) ?
C25 H25 . 0.95 ?
C26 C27 . 1.343(4) ?
C26 H26 . 0.95 ?
C27 C27A . 1.416(3) ?
C27 H27 . 0.95 ?
Mn1 Cl3 . 2.3577(7) y
Mn1 Cl4 . 2.3674(7) y
Mn1 Cl1 . 2.3725(7) y
Mn1 Cl2 . 2.3777(7) y
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C11 H11 Cl4 . 0.95 2.76 3.592(2) 146.4 yes
C13 H13 Cl1 2_665 0.95 2.66 3.422(2) 137.5 yes
C14 H14 Cl1 2_665 0.95 2.79 3.549(3) 137.2 yes
C21 H21 Cl3 1_465 0.95 2.80 3.632(2) 146.6 yes
C22 H22C Cl2 2_665 0.98 2.82 3.742(3) 156.3 yes
C23 H23 Cl1 1_565 0.95 2.81 3.440(3) 125.0 yes
C24 H24 Cl3 1_565 0.95 2.69 3.573(3) 154.4 yes
C27 H27 Cl4 2_666 0.95 2.77 3.600(3) 146.2 yes
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
C17A C11 N12 C13 . . . . -0.3(3) ?
C17A C11 N12 C12 . . . . -178.7(2) ?
C11 N12 C13 N13A . . . . 0.1(2) ?
C12 N12 C13 N13A . . . . 178.5(2) ?
N12 C13 N13A C17A . . . . 0.1(2) ?
N12 C13 N13A C14 . . . . -179.8(2) ?
C13 N13A C14 C15 . . . . -178.1(2) ?
C17A N13A C14 C15 . . . . 2.0(3) ?
N13A C14 C15 C16 . . . . -0.7(4) ?
C14 C15 C16 C17 . . . . -1.1(4) ?
C15 C16 C17 C17A . . . . 1.3(4) ?
N12 C11 C17A C17 . . . . -178.0(2) ?
N12 C11 C17A N13A . . . . 0.4(2) ?
C16 C17 C17A C11 . . . . 178.4(2) ?
C16 C17 C17A N13A . . . . 0.1(4) ?
C13 N13A C17A C11 . . . . -0.3(2) ?
C14 N13A C17A C11 . . . . 179.6(2) ?
C13 N13A C17A C17 . . . . 178.3(2) ?
C14 N13A C17A C17 . . . . -1.8(3) ?
C27A C21 N22 C23 . . . . 0.2(3) ?
C27A C21 N22 C22 . . . . -178.2(2) ?
C21 N22 C23 N23A . . . . -0.3(3) ?
C22 N22 C23 N23A . . . . 178.2(2) ?
N22 C23 N23A C24 . . . . -179.9(2) ?
N22 C23 N23A C27A . . . . 0.3(3) ?
C23 N23A C24 C25 . . . . -179.8(2) ?
C27A N23A C24 C25 . . . . 0.0(3) ?
N23A C24 C25 C26 . . . . -1.6(4) ?
C24 C25 C26 C27 . . . . 2.2(4) ?
C25 C26 C27 C27A . . . . -1.1(4) ?
N22 C21 C27A N23A . . . . 0.0(2) ?
N22 C21 C27A C27 . . . . 178.7(3) ?
C23 N23A C27A C21 . . . . -0.1(3) ?
C24 N23A C27A C21 . . . . 180.0(2) ?
C23 N23A C27A C27 . . . . -179.1(2) ?
C24 N23A C27A C27 . . . . 1.0(3) ?
C26 C27 C27A C21 . . . . -179.1(3) ?
C26 C27 C27A N23A . . . . -0.5(3) ?
