Hydrogen-bond-driven supramolecular helical assembly of a coumarin-substituted phthalonitrile derivative: synthesis and <i>in vitro</i> anticancer activity against colorectal adenocarcinoma
Topkan, Füsun; Özdemir, Mücahit; Özkan, Beyza Nur; Bozali, Kübra; Güler, Eray Metin; Zorlu, Yunus; Bulut, Mustafa; Görgülü, Ahmet Orhan; Yalçın, Bahattin; Acta Crystallographica Section D 78 (2022) –; doi:10.1107/S2059798322007823

data_2312028
_publ_section_title
;
 Hydrogen-bond-driven supramolecular helical assembly of a
 coumarin-substituted phthalonitrile derivative: synthesis and <i>in
 vitro</i> anticancer activity against colorectal adenocarcinoma
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section D'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2059798322007823
_journal_volume                  78
_journal_year                    2022
_chemical_formula_moiety         'C24 H22 N2 O3, [+ solvents]'
_chemical_formula_sum            'C24 H22 N2 O3'
_chemical_formula_weight         386.43
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   49.850(7)
_cell_length_b                   49.850(7)
_cell_length_c                   4.9234(8)
_cell_measurement_reflns_used    1475
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      18.66
_cell_measurement_theta_min      2.16
_cell_volume                     10596(3)
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0609
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       59
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -58
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            13237
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.124
_diffrn_reflns_theta_max         25.124
_diffrn_reflns_theta_min         0.817
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_description       plate
_exptl_crystal_F_000             3672
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4177
_refine_ls_number_restraints     290
_refine_ls_restrained_S_all      1.210
_refine_ls_R_factor_all          0.1993
_refine_ls_R_factor_gt           0.1095
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3201
_refine_ls_wR_factor_ref         0.3775
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1911
_reflns_number_total             4177
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            di5058sup1.cif
_cod_data_source_block           21gtu143_fs_2_0ma
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2312028
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C17A-C16A = C16A-C15A = C15A-C14 = C14-C13
 1.55 with sigma of 0.01
 C15A-C17A
 2.5 with sigma of 0.01
 C16A-C14
 2.5 with sigma of 0.01
 C14-C15A \\sim C14-C15B
 with sigma of 0.02
 C15A-C16A \\sim C15B-C16B
 with sigma of 0.02
 C16A-C17A \\sim C16B-C17B
 with sigma of 0.02
 C14-C16A \\sim C14-C16B
 with sigma of 0.04
 C15A-C17A \\sim C15B-C17B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.008 and sigma
for terminal atoms of 0.002 within 2A
4. Rigid body (RIGU) restrains
 C13, C14, C15A, C16A, C17A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C13, C14, C15B, C16B, C17B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(H14C)=Sof(H14D)=Sof(C15B)=Sof(H15C)=Sof(H15D)=Sof(C16B)=Sof(H16C)=
 Sof(H16D)=Sof(C17B)=Sof(H17D)=Sof(H17E)=Sof(H17F)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(C16A)=Sof(H16A)=
 Sof(H16B)=Sof(C17A)=Sof(H17A)=Sof(H17B)=Sof(H17C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C14(H14C,H14D), C15A(H15A,H15B), C15B(H15C,
 H15D), C16A(H16A,H16B), C16B(H16C,H16D)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C19(H19), C22(H22), C23(H23)
6.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C17A(H17A,H17B,H17C), C17B(H17D,
 H17E,H17F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              45611
_shelx_hkl_checksum              13654
_shelx_fab_checksum              73404
_olex2_submission_special_instructions 'No special instructions were received'