Photochemical [2 + 2] cycloadditions of naphthalene acrylic acids: templated and untemplated photoreactivity, selective homo/heterodimerizations, and conformational analysis
Temel, Merve; Yildiz, Gizem; Ceyhan, Kaan Berkay; Alkan, Fahri; Şahin, Onur; Türkmen, Yunus E.; RSC Advances 15 (2025) 24544–24556; doi:10.1039/D5RA03698D

data_7250680
_publ_section_title
;
 Photochemical [2 + 2] cycloadditions of naphthalene acrylic acids:
 templated and untemplated photoreactivity, selective
 homo/heterodimerizations, and conformational analysis
;
_journal_issue                   30
_journal_name_full               'RSC Advances'
_journal_page_first              24544
_journal_page_last               24556
_journal_paper_doi               10.1039/D5RA03698D
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C36 H24 O4'
_chemical_formula_sum            'C36 H24 O4'
_chemical_formula_weight         520.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-06-26 deposited with the CCDC.	2025-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.833(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9745(7)
_cell_length_b                   12.9911(10)
_cell_length_c                   13.0553(11)
_cell_measurement_reflns_used    9845
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.95
_cell_measurement_theta_min      2.25
_cell_volume                     1307.43(19)
_computing_cell_refinement       'SAINT(Bruker, 2013)'
_computing_data_collection       'APEX3 (Bruker, 2013)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Mercury (Macrae, 2020)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-3 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32579
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.421
_diffrn_reflns_theta_min         1.614
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 2232 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(1)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6499
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0403P)^2^+0.1857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                5508
_reflns_number_total             6499
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra03698d3.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7250680
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.988
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              28661