Computational and structural insights into the zwitterionic and neutral forms of N-substituted hydroxyformamidines in the solid state
Juma, David O.; Zamisa, Sizwe J.; Sharma, Anamika; Bongoza, Unathi; Njogu, Eric M.; Albericio, Fernando; Omondi, Bernard; CrystEngComm 27 (2025) 6508–6522; doi:10.1039/D5CE00521C

data_1575753
_publ_section_title
;
 Computational and structural insights into the zwitterionic and neutral
 forms of N-substituted hydroxyformamidines in the solid state
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              6508
_journal_page_last               6522
_journal_paper_doi               10.1039/D5CE00521C
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C13 H8 F4 N2 O'
_chemical_formula_sum            'C13 H8 F4 N2 O'
_chemical_formula_weight         284.21
_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             2025-04-09
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-05-19 deposited with the CCDC.	2025-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.932(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.5760(3)
_cell_length_b                   23.9624(8)
_cell_length_c                   13.8352(4)
_cell_measurement_reflns_used    9158
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      2.86
_cell_volume                     2466.05(15)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            95598
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         1.700
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1120 before and 0.0431 after correction.
The Ratio of minimum to maximum transmission is 0.9403.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0504P)^2^+0.6577P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1146
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4196
_reflns_number_total             5045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00521c1.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 1575752--1575753.cif.'
_cod_database_code               1575753
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C16(H16),
 C17(H17), C18(H18), C20(H20), C23(H23), C24(H24), C25(H25)
1.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_res_checksum              89082
_olex2_submission_special_instructions 'No special instructions were received'