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_7242838
_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_absolute_configuration ad
_chemical_formula_moiety         'C15 H14 Cl2 N2'
_chemical_formula_sum            'C15 H14 Cl2 N2'
_chemical_formula_weight         293.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-05-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-05-11 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 128.9840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.6079(3)
_cell_length_b                   42.6839(12)
_cell_length_c                   8.2782(2)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.52
_cell_volume                     2913.60(14)
_computing_cell_refinement       'COSMO (Bruker, V1.61, 2009)'
_computing_data_collection       'COSMO (Bruker, V1.61, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       56
_diffrn_reflns_limit_k_min       -53
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            32212
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.341
_diffrn_reflns_theta_min         0.954
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.433
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.868
_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    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_recrystallization_method
'The material was recrystallised from ethanol by slow evaporation'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 2368 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         6115
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0547P)^2^+2.4700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.827
_reflns_Friedel_fraction_max     0.692
_reflns_number_gt                5943
_reflns_number_total             6115
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00458a2.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 7242837--7242841.cif.'
_cod_database_code               7242838
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.878
_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 Aromatic/amide H refined with riding coordinates:
 N2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C7A(H7A), C10A(H10A), C11A(H11A),
 C13A(H13A), N2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B), C7B(H7B), C10B(H10B),
 C11B(H11B), C13B(H13B)
2.b Fitted hexagon refined as free rotating group:
 C1A(C2A,C3A,C4A,C5A,C6A), C8A(C9A,C10A,C11A,C13A,C14A), C1B(C2B,C3B,C4B,C5B,
 C6B), C8B(C9B,C10B,C11B,C13B,C14B)
2.c Idealised Me refined as rotating group:
 C15A(H15A,H15B,H15C), C16A(H16A,H16B,H16C), C15B(H15D,H15E,H15F), C16B(H16D,
 H16E,H16F)
;
_shelx_res_checksum              71476
_shelx_hkl_checksum              26557
_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'