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_2312029
_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         'C16 H20 O3'
_chemical_formula_sum            'C16 H20 O3'
_chemical_formula_weight         260.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_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                90
_cell_formula_units_Z            4
_cell_length_a                   29.189(8)
_cell_length_b                   5.5877(15)
_cell_length_c                   8.686(3)
_cell_measurement_reflns_used    1711
_cell_measurement_temperature    298
_cell_measurement_theta_max      22.62
_cell_measurement_theta_min      2.73
_cell_volume                     1416.7(7)
_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      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0565
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6701
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.395
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.083
_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    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 578 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2415
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0744
_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^)+(0.1144P)^2^+0.4608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1956
_refine_ls_wR_factor_ref         0.2111
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    0.923
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                1700
_reflns_number_total             2415
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            di5058sup1.cif
_cod_data_source_block           21gtu181_fs_1_0m
_cod_database_code               2312029
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.985
_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, All O(H) groups
2. Restrained distances
 C14-C13 = C15B-C14 = C15A-C14 = C16-C15B = C16-C15A = C17-C16
 1.55 with sigma of 0.01
 C14-C15A \\sim C14-C15B
 with sigma of 0.02
 C16-C15A \\sim C16-C15B
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C13, C14, C15A, C16, C17
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C13, C14, C15B, C16, C17
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(H14C)=Sof(H14D)=Sof(C15B)=Sof(H15C)=Sof(H15D)=Sof(H16C)=Sof(H16D)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(H16A)=Sof(H16B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C14(H14C,H14D), C15A(H15A,H15B), C15B(H15C,
 H15D), C16(H16A,H16B), C16(H16C,H16D)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6)
5.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C17(H17A,H17B,H17C)
5.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              31894
_shelx_hkl_checksum              57376
_olex2_submission_special_instructions 'No special instructions were received'