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_1575752
_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         '2(C25 H36 N2 O), C H2 Cl2'
_chemical_formula_sum            'C51 H74 Cl2 N4 O2'
_chemical_formula_weight         846.087
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_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                84.192(1)
_cell_angle_beta                 76.836(1)
_cell_angle_gamma                61.861(1)
_cell_formula_units_Z            2
_cell_length_a                   12.6939(3)
_cell_length_b                   13.0267(3)
_cell_length_c                   18.5039(5)
_cell_measurement_temperature    296.15
_cell_volume                     2627.18(12)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9744
_diffrn_measured_fraction_theta_max 0.9696
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.9744
_diffrn_reflns_Laue_measured_fraction_max 0.9696
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20842
_diffrn_reflns_point_group_measured_fraction_full 0.9744
_diffrn_reflns_point_group_measured_fraction_max 0.9696
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0879 before and 0.0407 after correction.
The Ratio of minimum to maximum transmission is 0.8837.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.070
_exptl_crystal_description       block
_exptl_crystal_F_000             917.046
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.6476
_refine_diff_density_min         -0.7286
_refine_diff_density_rms         0.0654
_refine_ls_d_res_high            0.8100
_refine_ls_d_res_low             10.9554
_refine_ls_goodness_of_fit_ref   1.0554
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    115
_refine_ls_number_parameters     549
_refine_ls_number_reflns         10046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0554
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0782
_refine_ls_shift/su_max          -0.0130
_refine_ls_shift/su_mean         0.0012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1455P)^2^+0.7101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2280
_refine_ls_wR_factor_ref         0.2677
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              16
_reflns_limit_k_min              -15
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                6418
_reflns_number_total             10046
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ce00521c1.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 1575752--1575753.cif.'
_cod_database_code               1575752
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C10(H10), C20(H20), C35(H35), C7(H7), C23(H23), C45(H45), C32(H32), C48(H48)
1.b Secondary CH2 refined with riding coordinates:
 C51(H51a,H51b)
1.c Aromatic/amide H refined with riding coordinates:
 N4(H4a), C13(H13), C38(H38), C3(H3), C18(H18), C5(H5), C4(H4), C28(H28),
 C17(H17), C29(H29), C16(H16), C43(H43), C30(H30), C41(H41), C42(H42)
1.d Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C37(H37a,H37b,H37c), C9(H9a,H9b,H9c), C8(H8a,H8b,H8c),
 C12(H12a,H12b,H12c), C11(H11a,H11b,H11c), C22(H22a,H22b,H22c), C36(H36a,H36b,
 H36c), C49(H49a,H49b,H49c), C50(H50a,H50b,H50c), C24(H24a,H24b,H24c), C33(H33a,
 H33b,H33c), C47(H47a,H47b,H47c), C25(H25a,H25b,H25c), C46(H46a,H46b,H46c),
 C34(H34a,H34b,H34c)
1.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'