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_1572908
_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         'C5 H6 N O, 1(Cl1)'
_chemical_formula_sum            'C5 H6 Cl N O'
_chemical_formula_weight         131.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2301(13)
_cell_length_b                   7.416(2)
_cell_length_c                   11.002(3)
_cell_measurement_reflns_used    1110
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      25.326
_cell_measurement_theta_min      3.372
_cell_volume                     589.9(2)
_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)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0809
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            674
_diffrn_reflns_point_group_measured_fraction_full 0.603
_diffrn_reflns_point_group_measured_fraction_max 0.603
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.326
_diffrn_reflns_theta_min         3.313
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_T_max  0.745207
_exptl_absorpt_correction_T_min  0.263470
_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 0.1594 before and 0.0953 after correction.
 The Ratio of minimum to maximum transmission is 0.36.

Final HKLF 4 output contains 6410 reflections, Rint = 0.1953
 (2497 with I > 3sig(I), Rint = 0.0809)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.145
_refine_diff_density_min         -1.027
_refine_diff_density_rms         0.194
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         674
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0933
_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^)+(0.1893P)^2^+0.3204P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2240
_refine_ls_wR_factor_ref         0.2335
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                621
_reflns_number_total             674
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06270a3.cif
_cod_data_source_block           OGH_D49_38
_cod_depositor_comments
'Adding full bibliography for 1572907--1572916.cif.'
_cod_database_code               1572908
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.934
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.98143
 0.01857
2. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(Cl3) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(Cl1) = Uanis(Cl2) = Uanis(Cl3)
3. Others
 Fixed Sof: Cl1(0.89) Cl2(0.06) Cl3(0.05)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C4(H4), C3(H3), C1(H1A)
4.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              20656
_shelx_hkl_checksum              7947
_olex2_submission_special_instructions 'No special instructions were received'