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_7246236
_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          'C19 H15 N O4'
_chemical_formula_moiety         'C19 H15 N O4'
_chemical_formula_sum            'C19 H15 N O4'
_chemical_formula_weight         321.32
_chemical_name_systematic
;
(3E,5E)-3-benzylidene-5-(4-nitrobenzylidene)dihydro-2H-pyran-4(3H)-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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                 90.5070(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5877(4)
_cell_length_b                   7.2192(4)
_cell_length_c                   28.0023(14)
_cell_measurement_reflns_used    2850
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.729
_cell_measurement_theta_min      1.454
_cell_volume                     1533.83(14)
_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      296(2)
_diffrn_detector_area_resol_mean 7.901
_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  0.0194
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            24896
_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         26.729
_diffrn_reflns_theta_min         1.454
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_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    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.375
_exptl_crystal_size_min          0.186
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0472P)^2^+0.5545P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1095
_reflns_number_gt                2850
_reflns_number_total             3262
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d2ra07681k2.cif
_cod_data_source_block           A1K7A11
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7246236
_shelx_shelxl_version_number     2019/2
_shelx_res_checksum              38623