Predicting molecular isomerism of symmetrical and unsymmetrical N,N′-diphenyl formamidines in the solid-state: crystal structure, Hirshfeld surface analysis, pairwise interaction energy, and ΔHfusion and ΔSfusion correlations
Zamisa, Sizwe J.; Bongoza, Unathi; Omondi, Bernard; CrystEngComm 23 (2021) 4459–4474; doi:10.1039/D1CE00458A

data_7242839
_publ_section_title
;
 Predicting molecular isomerism of symmetrical and unsymmetrical
 N,N&#x2032;-diphenyl formamidines in the solid-state: crystal structure,
 Hirshfeld surface analysis, pairwise interaction energy, and \DHfusion
 and \DSfusion correlations
;
_journal_issue                   25
_journal_name_full               CrystEngComm
_journal_page_first              4459
_journal_page_last               4474
_journal_paper_doi               10.1039/D1CE00458A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C19 H22 Cl2 N2'
_chemical_formula_sum            'C19 H22 Cl2 N2'
_chemical_formula_weight         349.28
_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             2019-01-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-03 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                75.198(2)
_cell_angle_beta                 77.861(3)
_cell_angle_gamma                63.236(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8974(6)
_cell_length_b                   9.9742(6)
_cell_length_c                   11.0128(7)
_cell_measurement_reflns_used    13205
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.470
_cell_measurement_theta_min      1.924
_cell_volume                     932.76(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13205
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.470
_diffrn_reflns_theta_min         1.924
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_recrystallization_method
'The material was recrystallised from ethanol by slow evaporation'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0477P)^2^+0.3767P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0904
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4230
_reflns_number_total             4573
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00458a2.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 7242837--7242841.cif.'
_cod_database_code               7242839
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.959
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), N2(H2)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C16(H16A,H16B,H16C), C15(H15A,H15B,
 H15C)
;
_shelx_res_checksum              87992
_shelx_hkl_checksum              68097
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'