Acid catalyzed one-pot approach towards the synthesis of curcuminoid systems: unsymmetrical diarylidene cycloalkanones, exploration of their single crystals, optical and nonlinear optical properties
Ali, Akbar; Din, Zia Ud; Ibrahim, Muhammad; Ashfaq, Muhammad; Muhammad, Shabbir; Gull, Dania; Tahir, Muhammad Nawaz; Rodrigues-Filho, Edson; Al-Sehemi, Abdullah G.; Suleman, Muhammad; RSC Advances 13 (2023) 4476–4494; doi:10.1039/D2RA07681K

data_7246237
_publ_section_title
;
 Acid catalyzed one-pot approach towards the synthesis of curcuminoid
 systems: unsymmetrical diarylidene cycloalkanones, exploration of their
 single crystals, optical and nonlinear optical properties
;
_journal_issue                   7
_journal_name_full               'RSC Advances'
_journal_page_first              4476
_journal_page_last               4494
_journal_paper_doi               10.1039/D2RA07681K
_journal_volume                  13
_journal_year                    2023
_chemical_formula_iupac          'C21 H20 O3'
_chemical_formula_moiety         'C21 H20 O3'
_chemical_formula_sum            'C21 H20 O3'
_chemical_formula_weight         320.37
_chemical_name_systematic
;
(2E,5E)-2-benzylidene-5-(2,3-dimethoxybenzylidene)cyclopentanone
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2022-05-11 deposited with the CCDC.	2023-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.154(2)
_cell_length_b                   6.9813(10)
_cell_length_c                   28.997(4)
_cell_measurement_reflns_used    2623
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.347
_cell_measurement_theta_min      1.404
_cell_volume                     3270.2(8)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-2019/2  (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.301
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            57033
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         1.404
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.345
_exptl_crystal_size_min          0.194
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0547
_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^)+(0.0146P)^2^+4.2071P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1161
_reflns_number_gt                2623
_reflns_number_total             2992
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d2ra07681k2.cif
_cod_data_source_block           A1K10A10
_cod_database_code               7246237
_shelx_shelxl_version_number     2019/2
_shelx_res_checksum              34769