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_1572914
_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         'Cl3, C11 H10 N O, C11 H9 N O'
_chemical_formula_sum            'C22 H19 Cl3 N2 O2'
_chemical_formula_weight         449.74
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                71.538(19)
_cell_angle_beta                 81.375(19)
_cell_angle_gamma                89.527(14)
_cell_formula_units_Z            2
_cell_length_a                   6.027(3)
_cell_length_b                   11.706(6)
_cell_length_c                   15.295(9)
_cell_measurement_reflns_used    506
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      22.591
_cell_measurement_theta_min      3.498
_cell_volume                     1011.1(9)
_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  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.974
_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  0.2284
_diffrn_reflns_av_unetI/netI     0.3770
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3636
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.393
_diffrn_reflns_theta_min         2.656
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.475
_exptl_absorpt_correction_T_max  0.745210
_exptl_absorpt_correction_T_min  0.522247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1189 before and 0.0843 after correction.
 The Ratio of minimum to maximum transmission is 0.70.

Final HKLF 4 output contains 17493 reflections, Rint = 0.2284
 (2031 with I > 3sig(I), Rint = 0.1017)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.387
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3636
_refine_ls_number_restraints     156
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.3614
_refine_ls_R_factor_gt           0.1321
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2983
_refine_ls_wR_factor_ref         0.4380
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1278
_reflns_number_total             3636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06270a3.cif
_cod_data_source_block           OGH_D49_27
_cod_depositor_comments
'Adding full bibliography for 1572907--1572916.cif.'
_cod_original_cell_volume        1011.1(10)
_cod_database_code               1572914
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.837
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.77152
 0.22848
2. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C21)
\\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C1) \\sim Ueq,
Uanis(C13) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C8) \\sim
Ueq, Uanis(C22) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C5) \\sim Ueq,
Uanis(C3) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C20) \\sim
Ueq, Uanis(N1) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C19) \\sim Ueq,
Uanis(C18) \\sim Ueq, : with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18), C7(H7), C22(H22), C4(H4), C11(H11), C21(H21), C9(H9),
 C8(H8), C1(H1A), C15(H15), C12(H12), C13(H13), C14(H14), C20(H20), C10(H10),
 C3(H3), C2(H2)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              3848
_shelx_hkl_checksum              78285
_olex2_submission_special_instructions 'No special instructions were received'