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_4519254
_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         'C14 H12 N4 O2, 2(C2 F3 O2)'
_chemical_formula_sum            'C18 H12 F6 N4 O6'
_chemical_formula_weight         494.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-13
_audit_creation_method
;
FinalCif V88 by Daniel Kratzert, Freiburg 2021,
https://github.com/dkratzert/FinalCif
;
_cell_angle_alpha                90
_cell_angle_beta                 99.146(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5863(3)
_cell_length_b                   11.2015(4)
_cell_length_c                   20.1697(7)
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    150
_cell_measurement_theta_max      57.053
_cell_measurement_theta_min      3.864
_cell_volume                     1915.25(12)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24671
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.308
_diffrn_reflns_theta_min         3.862
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.199771
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.85
_exptl_absorpt_coefficient_mu    0.948
_exptl_absorpt_correction_T_max  0.3063
_exptl_absorpt_correction_T_min  0.1995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1169 before and 0.0786 after correction.
The Ratio of minimum to maximum transmission is 0.6513.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light Yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         3925
_refine_ls_number_restraints     492
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0664
_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^)+(0.0896P)^2^+1.3651P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1721
_refine_ls_wR_factor_ref         0.1901
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2910
_reflns_number_total             3925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c05561_si_004.cif
_cod_data_source_block           ada1882
_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.

data item '_exptl_crystal_colour_primary' value 'Yellow' was changed
to 'yellow' 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               4519254
_shelx_shelxl_version_number     2018/3
_olex2_submission_special_instructions 'No special instructions were received'
_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
 C18A-F4A \\sim C18A-F5A \\sim C18A-F6A \\sim C18B-F4B \\sim C18B-F5B \\sim
C18B-F6B
 with sigma of 0.002
 F4A-F5A \\sim F5A-F6A \\sim F6A-F4A \\sim F4B-F5B \\sim F5B-F6B \\sim F6B-F4B
 with sigma of 0.02
 C16A-F1A \\sim C16A-F2A \\sim C16A-F3A \\sim C16B-F1B \\sim C16B-F2B \\sim
C16B-F3B
 with sigma of 0.002
 F1A-F2A \\sim F2A-F3A \\sim F3A-F1A \\sim F1B-F2B \\sim F2B-F3B \\sim F3B-F1B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F4A \\sim F5A \\sim F6A \\sim O5A \\sim O6A \\sim C17A \\sim C18A \\sim F4B
\\sim F5B \\sim F6B \\sim O5B \\sim O6B \\sim C17B \\sim C18B: within 2A with
sigma of 0.002 and sigma for terminal atoms of 0.02 within 2A
F1A \\sim F2A \\sim F3A \\sim O3A \\sim O4A \\sim C15A \\sim C16A \\sim F1B
\\sim F2B \\sim F3B \\sim O3B \\sim O4B \\sim C15B \\sim C16B: within 2A with
sigma of 0.002 and sigma for terminal atoms of 0.02 within 2A
4. Same fragment restrains
{F4A, F5A, F6A, O5A, O6A, C17A, C18A} sigma for 1-2: 0.001, 1-3: 0.04
as in
{F4B, F5B, F6B, O5B, O6B, C17B, C18B}
{F1A, F2A, F3A, O3A, O4A, C15A, C16A} sigma for 1-2: 0.001, 1-3: 0.04
as in
{F1B, F2B, F3B, O3B, O4B, C15B, C16B}
5. Others
 Sof(F4B)=Sof(F5B)=Sof(F6B)=Sof(O5B)=Sof(O6B)=Sof(C17B)=Sof(C18B)=1-FVAR(1)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(O5A)=Sof(O6A)=Sof(C17A)=Sof(C18A)=FVAR(1)
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(O3B)=Sof(O4B)=Sof(C15B)=Sof(C16B)=1-FVAR(2)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(O3A)=Sof(O4A)=Sof(C15A)=Sof(C16A)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), N4(H4), C2(H2A), C3(H3), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12),
 C14(H14)
6.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_res_checksum              61876
_shelx_hkl_checksum              23028