Hydrogen Bond Patterns of Dipyridone and Bis(Hydroxypyridinium) Cations
Mohan, Midhun; Essalhi, Mohamed; Zaye, Sarah; Rana, Love Karan; Maris, Thierry; Duong, Adam; ACS Omega 6 (2021) 35649–35656; doi:10.1021/acsomega.1c05561

data_4519252
_publ_section_title
;
 Hydrogen Bond Patterns of Dipyridone and Bis(Hydroxypyridinium) Cations
;
_journal_issue                   51
_journal_name_full               'ACS Omega'
_journal_page_first              35649
_journal_page_last               35656
_journal_paper_doi               10.1021/acsomega.1c05561
_journal_volume                  6
_journal_year                    2021
_chemical_formula_moiety         'C16 H14 N2 O2, 2(C2 F3 O2)'
_chemical_formula_sum            'C20 H14 F6 N2 O6'
_chemical_formula_weight         492.33
_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
_audit_creation_date             2021-09-16
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_cell_angle_alpha                92.229(7)
_cell_angle_beta                 102.919(6)
_cell_angle_gamma                103.078(6)
_cell_formula_units_Z            2
_cell_length_a                   10.3440(9)
_cell_length_b                   10.4190(11)
_cell_length_c                   10.5800(11)
_cell_measurement_reflns_used    2603
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.480
_cell_measurement_theta_min      4.306
_cell_volume                     1077.74(19)
_computing_cell_refinement
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16809
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.171
_diffrn_reflns_theta_min         4.306
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.65
_diffrn_source_power             0.02912
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           44.8
_exptl_absorpt_coefficient_mu    1.293
_exptl_absorpt_correction_T_max  0.6617
_exptl_absorpt_correction_T_min  0.5040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0959 before and 0.0490 after correction.
The Ratio of minimum to maximum transmission is 0.7617.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_description       platelet
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         3962
_refine_ls_number_restraints     624
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0661
_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^)+(0.1602P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2027
_refine_ls_wR_factor_ref         0.2128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2916
_reflns_number_total             3962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c05561_si_002.cif
_cod_data_source_block           ada242
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4519252
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.882
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 F1F-F2F \\sim F2F-F3F \\sim F3F-F1F
 with sigma of 0.002
 C2F-F1F \\sim C2F-F2F \\sim C2F-F3F
 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
C1F \\sim O1F \\sim O2F \\sim C2F \\sim F1F \\sim F2F \\sim F3F \\sim C1G \\sim
O1G \\sim O2G \\sim C2G \\sim F1G \\sim F2G \\sim F3G \\sim C1C \\sim O1C \\sim
O2C \\sim C2C \\sim F1C \\sim F2C \\sim F3C \\sim C1D \\sim O1D \\sim O2D \\sim
C2D \\sim F1D \\sim F2D \\sim F3D: within 1.7A with sigma of 0.001 and sigma
for terminal atoms of 0.02 within 1.7A
4. Rigid body (RIGU) restrains
 C1C, O1C, O2C, C2C, F1C, F2C, F3C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1D, O1D, O2D, C2D, F1D, F2D, F3D
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1F, O1F, O2F, C2F, F1F, F2F, F3F
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1G, O1G, O2G, C2G, F1G, F2G, F3G
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Same fragment restrains
{C1F, O1F, O2F, C2F, F1F, F2F, F3F} sigma for 1-2: 0.001, 1-3: 0.04
as in
{C1G, O1G, O2G, C2G, F1G, F2G, F3G}
{C1F, O1F, O2F, C2F, F1F, F2F, F3F} sigma for 1-2: 0.001, 1-3: 0.04
as in
{C1C, O1C, O2C, C2C, F1C, F2C, F3C}
{C1F, O1F, O2F, C2F, F1F, F2F, F3F} sigma for 1-2: 0.001, 1-3: 0.04
as in
{C1D, O1D, O2D, C2D, F1D, F2D, F3D}
6. Others
 Sof(C1G)=Sof(O1G)=Sof(O2G)=Sof(C2G)=Sof(F1G)=Sof(F2G)=Sof(F3G)=1-FVAR(1)
 Sof(C1F)=Sof(O1F)=Sof(O2F)=Sof(C2F)=Sof(F1F)=Sof(F2F)=Sof(F3F)=FVAR(1)
 Sof(C1D)=Sof(O1D)=Sof(O2D)=Sof(C2D)=Sof(F1D)=Sof(F2D)=Sof(F3D)=1-FVAR(2)
 Sof(C1C)=Sof(O1C)=Sof(O2C)=Sof(C2C)=Sof(F1C)=Sof(F2C)=Sof(F3C)=FVAR(2)
7.a Aromatic/amide H refined with riding coordinates:
 N1A(H1AA), C2A(H2A), C3A(H3A), C5A(H5A), C7A(H7A), C8A(H8A), N1B(H1BA),
 C2B(H2B), C3B(H3B), C5B(H5B), C7B(H7B), C8B(H8B)
7.b Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1B(H1B)
;
_shelx_res_checksum              55252
_shelx_hkl_checksum              5089
_olex2_submission_special_instructions 'No special instructions were received'