Dichlorine-pyridine <i>N</i>-oxide halogen-bonded complexes.
Limberg, Niklas; Rautiainen, J. Mikko; Lundell, Jan; Riedel, Sebastian; Rissanen, Kari; Puttreddy, Rakesh; Chemical science 15 (2024) 18840–18845; doi:10.1039/d4sc06270a

data_1572915
_publ_section_title
;
 Dichlorine-pyridine <i>N</i>-oxide halogen-bonded complexes.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              18840
_journal_page_last               18845
_journal_paper_doi               10.1039/d4sc06270a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'Cl2, C5 H5 N O'
_chemical_formula_sum            'C5 H5 Cl2 N O'
_chemical_formula_weight         166.00
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-09-11
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-13 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.221(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   13.8648(10)
_cell_length_b                   13.7600(8)
_cell_length_c                   16.1649(15)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.280
_cell_measurement_theta_min      2.785
_cell_volume                     2789.9(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28774
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_min         2.197
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1824 before and 0.0999 after correction.
The Ratio of minimum to maximum transmission is 0.7377.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.554
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.282
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.276
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0758
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1189P)^2^+27.3423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2460
_refine_ls_wR_factor_ref         0.2593
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2165
_reflns_number_total             2555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06270a3.cif
_cod_data_source_block           OGH_D49_57
_cod_depositor_comments
'Adding full bibliography for 1572907--1572916.cif.'
_cod_database_code               1572915
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.895
_shelx_estimated_absorpt_t_min   0.653
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.84856
 0.15144
2. Restrained distances
 O1A-N1A \\sim O1B-N1B
 with sigma of 0.02
 N1A-C5A \\sim N1B-C5B
 with sigma of 0.02
 N1A-C1A \\sim N1B-C1B
 with sigma of 0.02
 C5A-C4A \\sim C5B-C4B
 with sigma of 0.02
 C1A-C2A \\sim C1B-C2B
 with sigma of 0.02
 C4A-C3A \\sim C4B-C3B
 with sigma of 0.02
 C3A-C2A \\sim C3B-C2B
 with sigma of 0.02
 O1A-C5A \\sim O1B-C5B
 with sigma of 0.04
 O1A-C1A \\sim O1B-C1B
 with sigma of 0.04
 N1A-C4A \\sim N1B-C4B
 with sigma of 0.04
 N1A-C2A \\sim N1B-C2B
 with sigma of 0.04
 C5A-C1A \\sim C5B-C1B
 with sigma of 0.04
 C5A-C3A \\sim C5B-C3B
 with sigma of 0.04
 C1A-C3A \\sim C1B-C3B
 with sigma of 0.04
 C4A-C2A \\sim C4B-C2B
 with sigma of 0.04
 O2A-N2A \\sim O2B-N2B
 with sigma of 0.02
 N2A-C6A \\sim N2B-C6B
 with sigma of 0.02
 N2A-C10A \\sim N2B-C10B
 with sigma of 0.02
 C6A-C7A \\sim C6B-C7B
 with sigma of 0.02
 C10A-C9A \\sim C10B-C9B
 with sigma of 0.02
 C9A-C8A \\sim C9B-C8B
 with sigma of 0.02
 C7A-C8A \\sim C7B-C8B
 with sigma of 0.02
 O2A-C6A \\sim O2B-C6B
 with sigma of 0.04
 O2A-C10A \\sim O2B-C10B
 with sigma of 0.04
 N2A-C9A \\sim N2B-C9B
 with sigma of 0.04
 N2A-C7A \\sim N2B-C7B
 with sigma of 0.04
 C6A-C10A \\sim C6B-C10B
 with sigma of 0.04
 C6A-C8A \\sim C6B-C8B
 with sigma of 0.04
 C10A-C8A \\sim C10B-C8B
 with sigma of 0.04
 C9A-C7A \\sim C9B-C7B
 with sigma of 0.04
 Cl4A-Cl3A \\sim Cl3B-Cl4B
 with sigma of 0.02
3. Restrained planarity
 O1B, N1B, C5B, C1B, C2B, C3B, C4B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(Cl2A) = Uanis(Cl4B) = Uanis(Cl2B) = Uanis(Cl3A) = Uanis(Cl3B) =
Uanis(Cl4A) = Uanis(Cl1B) = Uanis(Cl1A)
Uanis(C1B) = Uanis(C5A) = Uanis(C4A) = Uanis(C5B) = Uanis(C4B) = Uanis(C3A) =
Uanis(C3B) = Uanis(C2A) = Uanis(C2B) = Uanis(C1A)
Uanis(N1A) = Uanis(N1B)
Uanis(O1A) = Uanis(O1B)
Uanis(C10B) = Uanis(C9B) = Uanis(C10A) = Uanis(C8B) = Uanis(C9A) = Uanis(C7B) =
Uanis(C8A) = Uanis(C7A) = Uanis(C6B) = Uanis(C6A)
Uanis(N2B) = Uanis(N2A)
Uanis(O2B) = Uanis(O2A)
5. Others
 Fixed Sof: Cl2A(0.95) Cl3A(0.95) Cl4A(0.95) Cl1A(0.95) O1A(0.95) O2A(0.95)
 N1A(0.95) N2A(0.95) C5A(0.95) H5A(0.95) C6A(0.95) H6A(0.95) C10A(0.95)
 H10A(0.95) C1A(0.95) H1A(0.95) C9A(0.95) H9A(0.95) C7A(0.95) H7A(0.95)
 C4A(0.95) H4A(0.95) C8A(0.95) H8A(0.95) C3A(0.95) H3A(0.95) C2A(0.95)
 H2A(0.95) Cl4B(0.05) Cl3B(0.05) Cl2B(0.05) Cl1B(0.05) O1B(0.05) C3B(0.05)
 H3B(0.05) C4B(0.05) H4B(0.05) C5B(0.05) H5B(0.05) N1B(0.05) C1B(0.05)
 H1B(0.05) C2B(0.05) H2B(0.05) C10B(0.05) H10B(0.05) O2B(0.05) N2B(0.05)
 C6B(0.05) H6B(0.05) C9B(0.05) H9B(0.05) C7B(0.05) H7B(0.05) C8B(0.05) H8B(0.05)
6.a Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C6A(H6A), C10A(H10A), C1A(H1A), C9A(H9A), C7A(H7A), C4A(H4A),
 C8A(H8A), C3A(H3A), C2A(H2A), C3B(H3B), C4B(H4B), C5B(H5B), C1B(H1B), C2B(H2B),
  C10B(H10B), C6B(H6B), C9B(H9B), C7B(H7B), C8B(H8B)
6.b Fitted hexagon refined as free rotating group:
 C3B(C4B,C5B,N1B,C1B,C2B)
;
_shelx_res_checksum              69647
_shelx_hkl_checksum              5517
_olex2_submission_special_instructions 'No special instructions were received'