#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:01:11 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281384 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/84/1568409.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1568409
loop_
_publ_author_name
'Pröhm, Patrick'
'Berg, Willi'
'Rupf, Susanne Margot'
'Müller, Carsten'
'Riedel, Sebastian'
_publ_section_title
;
 On pyridine chloronium cations
;
_journal_issue                   9
_journal_name_full               'Chemical Science'
_journal_page_first              2325
_journal_page_last               2329
_journal_paper_doi               10.1039/D2SC06757A
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         '0.5(C14 H18 Cl2 N2), Cl3, 0.5(C14 H18 N2)'
_chemical_formula_sum            'C14 H18 Cl4 N2'
_chemical_formula_weight         356.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-03
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2022-11-30 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.077(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3507(10)
_cell_length_b                   6.7026(6)
_cell_length_c                   15.1667(17)
_cell_measurement_reflns_used    4471
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.56
_cell_volume                     823.41(15)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7667
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.354
_diffrn_reflns_theta_min         2.559
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0628 before and 0.0443 after correction.
The Ratio of minimum to maximum transmission is 0.8867.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0312P)²+0.2456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0680
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1997
_reflns_number_total             2197
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc06757a2.cif
_cod_data_source_block           p21_m_final
_cod_depositor_comments
'Adding full bibliography for 1568406--1568411.cif.'
_cod_database_code               1568409
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.789
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H15A(0.5) H15B(0.5) H15C(0.5) H16A(0.5) H16B(0.5) H16C(0.5)
 H25A(0.5) H25B(0.5) H25C(0.5) H26A(0.5) H26B(0.5) H26C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C21(H21), C22(H22), C23(H23)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.45975(5) 0.750000 0.28838(2) 0.01426(10) Uani 1 2 d S T P . .
Cl2 Cl 0.51385(5) 0.250000 0.18771(2) 0.01764(11) Uani 1 2 d S T P . .
Cl3 Cl 0.79788(6) 0.250000 0.24099(3) 0.02566(12) Uani 1 2 d S T P . .
Cl4 Cl 0.23700(6) 0.250000 0.13511(3) 0.02489(12) Uani 1 2 d S T P . .
N1 N 0.34722(17) 0.750000 0.17261(9) 0.0140(3) Uani 1 2 d S T P . .
N2 N 0.61134(17) 0.750000 0.44461(9) 0.0137(3) Uani 1 2 d S T P . .
C10 C 0.1797(2) 0.750000 0.15488(11) 0.0171(3) Uani 1 2 d S T P . .
C11 C 0.0914(2) 0.750000 0.06506(11) 0.0213(4) Uani 1 2 d S T P . .
H11 H -0.025837 0.750000 0.050644 0.026 Uiso 1 2 calc R U P . .
C12 C 0.1739(2) 0.750000 -0.00406(12) 0.0243(4) Uani 1 2 d S T P . .
H12 H 0.113530 0.750000 -0.065849 0.029 Uiso 1 2 calc R U P . .
C13 C 0.3443(2) 0.750000 0.01759(11) 0.0221(4) Uani 1 2 d S T P . .
H13 H 0.400828 0.750000 -0.029704 0.027 Uiso 1 2 calc R U P . .
C14 C 0.4336(2) 0.750000 0.10712(11) 0.0171(3) Uani 1 2 d S T P . .
C15 C 0.6176(2) 0.750000 0.13330(11) 0.0187(3) Uani 1 2 d S T P . .
H15A H 0.656868 0.863905 0.173208 0.028 Uiso 0.5 1 calc R U P A -1
H15B H 0.659661 0.760287 0.078532 0.028 Uiso 0.5 1 calc R U P A -1
H15C H 0.657099 0.625808 0.165366 0.028 Uiso 0.5 1 calc R U P A -1
C16 C 0.0973(2) 0.750000 0.23185(12) 0.0221(4) Uani 1 2 d S T P . .
H16A H 0.114002 0.620385 0.262631 0.033 Uiso 0.5 1 calc R U P B -1
H16B H -0.021187 0.774163 0.208435 0.033 Uiso 0.5 1 calc R U P B -1
H16C H 0.144979 0.855452 0.275049 0.033 Uiso 0.5 1 calc R U P B -1
C20 C 0.7775(2) 0.750000 0.46410(11) 0.0155(3) Uani 1 2 d S T P . .
C21 C 0.8719(2) 0.750000 0.55332(11) 0.0179(3) Uani 1 2 d S T P . .
H21 H 0.989023 0.750000 0.565855 0.021 Uiso 1 2 calc R U P . .
C22 C 0.7925(2) 0.750000 0.62385(11) 0.0187(3) Uani 1 2 d S T P . .
H22 H 0.854601 0.750000 0.685301 0.022 Uiso 1 2 calc R U P . .
C23 C 0.6217(2) 0.750000 0.60343(11) 0.0179(3) Uani 1 2 d S T P . .
H23 H 0.565092 0.750000 0.650724 0.021 Uiso 1 2 calc R U P . .
C24 C 0.5336(2) 0.750000 0.51263(11) 0.0150(3) Uani 1 2 d S T P . .
C25 C 0.3484(2) 0.750000 0.48794(11) 0.0181(3) Uani 1 2 d S T P . .
H25A H 0.308027 0.620501 0.461676 0.027 Uiso 0.5 1 calc R U P C -1
H25B H 0.307988 0.855670 0.443431 0.027 Uiso 0.5 1 calc R U P C -1
H25C H 0.308201 0.773829 0.542584 0.027 Uiso 0.5 1 calc R U P C -1
C26 C 0.8577(2) 0.750000 0.38520(12) 0.0201(3) Uani 1 2 d S T P . .
H26A H 0.977116 0.731996 0.407784 0.030 Uiso 0.5 1 calc R U P D -1
H26B H 0.835684 0.877361 0.352768 0.030 Uiso 0.5 1 calc R U P D -1
H26C H 0.812398 0.640643 0.343710 0.030 Uiso 0.5 1 calc R U P 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 0.0000 0.0000 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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_3
_geom_angle_publ_flag
Cl4 Cl2 Cl3 179.74(2) . . ?
C10 N1 Cl1 117.81(11) . . ?
C10 N1 C14 123.93(14) . . ?
C14 N1 Cl1 118.26(12) . . ?
C24 N2 C20 119.69(14) . . ?
N1 C10 C11 118.12(15) . . ?
N1 C10 C16 119.57(14) . . ?
C11 C10 C16 122.30(16) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.08(17) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.52(16) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.87(16) . . ?
C14 C13 H13 119.6 . . ?
N1 C14 C13 117.49(16) . . ?
N1 C14 C15 120.01(14) . . ?
C13 C14 C15 122.50(15) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C20 C21 121.56(15) . . ?
N2 C20 C26 117.32(14) . . ?
C21 C20 C26 121.12(15) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 C20 119.07(16) . . ?
C22 C21 H21 120.5 . . ?
C21 C22 H22 120.4 . . ?
C23 C22 C21 119.13(15) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 H23 120.4 . . ?
C22 C23 C24 119.23(15) . . ?
C24 C23 H23 120.4 . . ?
N2 C24 C23 121.33(15) . . ?
N2 C24 C25 117.97(14) . . ?
C23 C24 C25 120.70(15) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C20 C26 H26A 109.5 . . ?
C20 C26 H26B 109.5 . . ?
C20 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
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 N1 1.7786(13) . ?
Cl2 Cl3 2.3123(7) . ?
Cl2 Cl4 2.2547(7) . ?
N1 C10 1.359(2) . ?
N1 C14 1.362(2) . ?
N2 C20 1.347(2) . ?
N2 C24 1.346(2) . ?
C10 C11 1.382(2) . ?
C10 C16 1.492(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(2) . ?
C14 C15 1.490(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C20 C21 1.390(2) . ?
C20 C26 1.507(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.395(2) . ?
C24 C25 1.500(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 N1 C10 C11 180.000(0) . . . . ?
Cl1 N1 C10 C16 0.000(0) . . . . ?
Cl1 N1 C14 C13 180.000(0) . . . . ?
Cl1 N1 C14 C15 0.000(0) . . . . ?
N1 C10 C11 C12 0.000(0) . . . . ?
N2 C20 C21 C22 0.000(1) . . . . ?
C10 N1 C14 C13 0.000(0) . . . . ?
C10 N1 C14 C15 180.000(0) . . . . ?
C10 C11 C12 C13 0.000(0) . . . . ?
C11 C12 C13 C14 0.000(0) . . . . ?
C12 C13 C14 N1 0.000(0) . . . . ?
C12 C13 C14 C15 180.000(0) . . . . ?
C14 N1 C10 C11 0.000(0) . . . . ?
C14 N1 C10 C16 180.000(0) . . . . ?
C16 C10 C11 C12 180.000(0) . . . . ?
C20 N2 C24 C23 0.000(1) . . . . ?
C20 N2 C24 C25 180.000(0) . . . . ?
C20 C21 C22 C23 0.000(1) . . . . ?
C21 C22 C23 C24 0.000(1) . . . . ?
C22 C23 C24 N2 0.000(1) . . . . ?
C22 C23 C24 C25 180.000(1) . . . . ?
C24 N2 C20 C21 0.000(1) . . . . ?
C24 N2 C20 C26 180.000(0) . . . . ?
C26 C20 C21 C22 180.000(1) . . . . ?
