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_4519253
_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         'C15 H11 N3 O2, 2(H2 O1)'
_chemical_formula_sum            'C15 H15 N3 O4'
_chemical_formula_weight         301.30
_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   mixed
_atom_sites_solution_primary     dual
_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                90
_cell_angle_beta                 104.613(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.2786(15)
_cell_length_b                   3.7845(5)
_cell_length_c                   14.1350(17)
_cell_measurement_reflns_used    1144
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      72.566
_cell_measurement_theta_min      6.892
_cell_volume                     687.35(15)
_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)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker AXS D8 Discovery'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8690
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.566
_diffrn_reflns_theta_min         6.892
_exptl_absorpt_coefficient_mu    0.900
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1344
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0654
_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^)+(0.1141P)^2^+0.2080P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.1995
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1144
_reflns_number_total             1344
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c05561_si_003.cif
_cod_data_source_block           2011734
_cod_database_code               4519253
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.840
_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,H) groups
2. Shared sites
{N9, C9}
3. Restrained distances
 O1W-H1WA = O1W-H1WB
 0.85 with sigma of 0.002
 H1WA-H1WA_$1
 2.3 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(N9) = Uanis(C9)
5. Others
 Fixed Sof: N9(0.5) C9(0.5) H9(0.5) O1W(0.89) H1WA(0.89) H1WB(0.89) O2W(0.11)
 H2WA(0.11) H2WB(0.11)
6.a Riding coordinates:
 O2W(H2WA,H2WB)
6.b Aromatic/amide H refined with riding coordinates:
 C10(H10), N3(H3), C4(H4), C6(H6), C7(H7), C9(H9)
;
_shelx_res_checksum              9208
_shelx_hkl_checksum              97673
_olex2_submission_special_instructions 'No special instructions were received'