#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:06:55 +0300 (Fri, 05 May 2023) $
#$Revision: 283421 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/22/7062293.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7062293
loop_
_publ_author_name
'Nizar, Siti Nabilla Aliya Mohd'
'Rosli, Mohd Mustaqim'
'Samsuri, Siti Azrah Mohamad'
'Razak, Ibrahim Abdul'
'Arshad, Suhana'
_publ_section_title
;
 Involvement of halogen and polyaromatic substituents in chalcone
 derivatives as dye sensitizers in solar cell applications
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5804
_journal_page_last               5815
_journal_paper_doi               10.1039/D2NJ05937A
_journal_volume                  47
_journal_year                    2023
_chemical_formula_sum            'C26 H17 F O2'
_chemical_formula_weight         380.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-05-05 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                97.824(8)
_cell_angle_beta                 102.058(7)
_cell_angle_gamma                98.891(7)
_cell_formula_units_Z            2
_cell_length_a                   7.506(4)
_cell_length_b                   9.968(5)
_cell_length_c                   12.308(6)
_cell_measurement_reflns_used    1003
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.61
_cell_measurement_theta_min      2.47
_cell_volume                     876.1(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0978
_diffrn_reflns_av_unetI/netI     0.0957
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20756
_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         25.999
_diffrn_reflns_theta_min         1.718
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.572
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1670
_refine_ls_R_factor_gt           0.0705
_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/[σ²(Fo²)+(0.0792P)²+0.3509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1646
_refine_ls_wR_factor_ref         0.2311
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1512
_reflns_number_total             3449
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj05937a2.cif
_cod_data_source_block           mo_SNA02_1_0m
_cod_depositor_comments
'Adding full bibliography for 7062293--7062294.cif.'
_cod_original_cell_volume        876.1(7)
_cod_database_code               7062293
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.946
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.9595(4) 0.4976(2) 0.71861(18) 0.0916(8) Uani 1 1 d . . . . .
O1 O 0.6998(5) 0.8153(3) 0.4880(3) 0.1062(12) Uani 1 1 d . . . . .
O2 O 0.8618(4) 0.2515(3) 0.6000(2) 0.0770(8) Uani 1 1 d . . . . .
C1 C 0.3921(5) 0.7074(4) 0.0671(3) 0.0648(10) Uani 1 1 d . . . . .
H1A H 0.4288 0.6255 0.0819 0.078 Uiso 1 1 calc R U . . .
C2 C 0.3169(5) 0.7174(4) -0.0403(3) 0.0659(11) Uani 1 1 d . . . . .
H2A H 0.3021 0.6426 -0.0977 0.079 Uiso 1 1 calc R U . . .
C3 C 0.2613(5) 0.8378(4) -0.0660(3) 0.0581(10) Uani 1 1 d . . . . .
C4 C 0.1840(5) 0.8523(5) -0.1781(3) 0.0683(11) Uani 1 1 d . . . . .
H4A H 0.1699 0.7790 -0.2366 0.082 Uiso 1 1 calc R U . . .
C5 C 0.1314(5) 0.9679(5) -0.2015(3) 0.0701(11) Uani 1 1 d . . . . .
H5A H 0.0808 0.9737 -0.2760 0.084 Uiso 1 1 calc R U . . .
C6 C 0.1501(5) 1.0827(4) -0.1162(3) 0.0619(10) Uani 1 1 d . . . . .
C7 C 0.0966(5) 1.2045(5) -0.1378(4) 0.0725(12) Uani 1 1 d . . . . .
H7A H 0.0463 1.2126 -0.2118 0.087 Uiso 1 1 calc R U . . .
C8 C 0.1156(6) 1.3142(5) -0.0530(4) 0.0770(12) Uani 1 1 d . . . . .
H8A H 0.0794 1.3955 -0.0700 0.092 Uiso 1 1 calc R U . . .
C9 C 0.1872(5) 1.3038(4) 0.0555(4) 0.0703(11) Uani 1 1 d . . . . .
H9A H 0.2000 1.3784 0.1127 0.084 Uiso 1 1 calc R U . . .
C10 C 0.2412(5) 1.1837(4) 0.0822(3) 0.0595(10) Uani 1 1 d . . . . .
C11 C 0.3151(5) 1.1680(4) 0.1941(3) 0.0642(11) Uani 1 1 d . . . . .
H11A H 0.3258 1.2406 0.2526 0.077 Uiso 1 1 calc R U . . .
C12 C 0.3699(5) 1.0526(4) 0.2184(3) 0.0632(10) Uani 1 1 d . . . . .
H12A H 0.4183 1.0473 0.2933 0.076 Uiso 1 1 calc R U . . .
C13 C 0.3571(5) 0.9368(4) 0.1336(3) 0.0536(9) Uani 1 1 d . . . . .
C14 C 0.2810(4) 0.9486(4) 0.0220(3) 0.0503(9) Uani 1 1 d . . . . .
C15 C 0.2240(4) 1.0718(4) -0.0041(3) 0.0542(9) Uani 1 1 d . . . . .
C16 C 0.4167(5) 0.8149(4) 0.1561(3) 0.0558(10) Uani 1 1 d . . . . .
C17 C 0.5068(5) 0.8023(4) 0.2688(3) 0.0662(11) Uani 1 1 d . . . . .
H17A H 0.5208 0.8799 0.3234 0.079 Uiso 1 1 calc R U . . .
C18 C 0.5713(6) 0.7000(4) 0.3058(3) 0.0711(11) Uani 1 1 d . . . . .
H18A H 0.5573 0.6186 0.2552 0.085 Uiso 1 1 calc R U . . .
C19 C 0.6639(5) 0.7063(4) 0.4222(3) 0.0660(11) Uani 1 1 d . . . . .
C20 C 0.7156(5) 0.5832(4) 0.4631(3) 0.0542(9) Uani 1 1 d . . . . .
C21 C 0.8169(5) 0.5961(4) 0.5721(3) 0.0613(10) Uani 1 1 d . . . . .
H21A H 0.8559 0.6826 0.6176 0.074 Uiso 1 1 calc R U . . .
C22 C 0.8593(5) 0.4841(4) 0.6127(3) 0.0622(10) Uani 1 1 d . . . . .
C23 C 0.8064(5) 0.3539(4) 0.5496(3) 0.0583(10) Uani 1 1 d . . . . .
C24 C 0.7063(5) 0.3410(4) 0.4419(3) 0.0653(11) Uani 1 1 d . . . . .
H24A H 0.6676 0.2541 0.3971 0.078 Uiso 1 1 calc R U . . .
C25 C 0.6615(5) 0.4538(4) 0.3986(3) 0.0629(10) Uani 1 1 d . . . . .
H25A H 0.5935 0.4428 0.3245 0.076 Uiso 1 1 calc R U . . .
C26 C 0.8047(7) 0.1157(4) 0.5374(4) 0.0950(15) Uani 1 1 d . . . . .
H26A H 0.8464 0.0516 0.5840 0.143 Uiso 1 1 calc R U . . .
H26B H 0.8573 0.1089 0.4726 0.143 Uiso 1 1 calc R U . . .
H26C H 0.6718 0.0947 0.5133 0.143 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 O2 C26 117.4(3) . . ?
C2 C1 C16 122.3(4) . . ?
C2 C1 H1A 118.8 . . ?
C16 C1 H1A 118.8 . . ?
C1 C2 C3 120.7(4) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C2 C3 C14 118.9(3) . . ?
C2 C3 C4 122.1(4) . . ?
C14 C3 C4 119.0(4) . . ?
C5 C4 C3 121.5(4) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C4 C5 C6 121.7(4) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C7 C6 C15 118.4(4) . . ?
C7 C6 C5 123.1(4) . . ?
C15 C6 C5 118.5(4) . . ?
C8 C7 C6 121.8(4) . . ?
C8 C7 H7A 119.1 . . ?
C6 C7 H7A 119.1 . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C10 120.8(4) . . ?
C8 C9 H9A 119.6 . . ?
C10 C9 H9A 119.6 . . ?
C9 C10 C15 119.6(4) . . ?
C9 C10 C11 122.7(4) . . ?
C15 C10 C11 117.7(4) . . ?
C12 C11 C10 122.0(4) . . ?
C12 C11 H11A 119.0 . . ?
C10 C11 H11A 119.0 . . ?
C11 C12 C13 122.3(4) . . ?
C11 C12 H12A 118.9 . . ?
C13 C12 H12A 118.9 . . ?
C14 C13 C16 119.4(3) . . ?
C14 C13 C12 116.9(3) . . ?
C16 C13 C12 123.7(3) . . ?
C13 C14 C3 120.1(3) . . ?
C13 C14 C15 120.9(3) . . ?
C3 C14 C15 119.0(3) . . ?
C6 C15 C10 119.5(4) . . ?
C6 C15 C14 120.3(3) . . ?
C10 C15 C14 120.2(3) . . ?
C1 C16 C13 118.6(3) . . ?
C1 C16 C17 120.4(4) . . ?
C13 C16 C17 121.0(3) . . ?
C18 C17 C16 130.1(4) . . ?
C18 C17 H17A 115.0 . . ?
C16 C17 H17A 115.0 . . ?
C17 C18 C19 122.9(4) . . ?
C17 C18 H18A 118.6 . . ?
C19 C18 H18A 118.6 . . ?
O1 C19 C18 120.0(4) . . ?
O1 C19 C20 119.1(4) . . ?
C18 C19 C20 120.9(4) . . ?
C25 C20 C21 118.1(3) . . ?
C25 C20 C19 122.8(4) . . ?
C21 C20 C19 119.0(3) . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21A 120.0 . . ?
C20 C21 H21A 120.0 . . ?
F1 C22 C21 119.6(3) . . ?
F1 C22 C23 117.6(3) . . ?
C21 C22 C23 122.7(4) . . ?
O2 C23 C24 126.2(3) . . ?
O2 C23 C22 116.4(3) . . ?
C24 C23 C22 117.4(4) . . ?
C23 C24 C25 121.0(4) . . ?
C23 C24 H24A 119.5 . . ?
C25 C24 H24A 119.5 . . ?
C24 C25 C20 120.8(4) . . ?
C24 C25 H25A 119.6 . . ?
C20 C25 H25A 119.6 . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C22 1.340(4) . ?
O1 C19 1.220(4) . ?
O2 C23 1.340(4) . ?
O2 C26 1.416(5) . ?
C1 C2 1.347(5) . ?
C1 C16 1.385(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.385(5) . ?
C2 H2A 0.9300 . ?
C3 C14 1.404(5) . ?
C3 C4 1.417(5) . ?
C4 C5 1.323(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.412(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.378(5) . ?
C6 C15 1.401(5) . ?
C7 C8 1.372(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.356(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.381(5) . ?
C9 H9A 0.9300 . ?
C10 C15 1.402(5) . ?
C10 C11 1.413(5) . ?
C11 C12 1.331(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.423(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.402(5) . ?
C13 C16 1.401(5) . ?
C14 C15 1.417(5) . ?
C16 C17 1.442(5) . ?
C17 C18 1.292(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.444(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.464(5) . ?
C20 C25 1.372(5) . ?
C20 C21 1.375(5) . ?
C21 C22 1.340(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.372(5) . ?
C23 C24 1.358(5) . ?
C24 C25 1.366(5) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C1 C2 C3 0.3(6) . . . . ?
C1 C2 C3 C14 -1.3(5) . . . . ?
C1 C2 C3 C4 179.1(3) . . . . ?
C2 C3 C4 C5 180.0(4) . . . . ?
C14 C3 C4 C5 0.4(5) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C4 C5 C6 C7 -180.0(4) . . . . ?
C4 C5 C6 C15 -0.9(6) . . . . ?
C15 C6 C7 C8 0.6(6) . . . . ?
C5 C6 C7 C8 179.6(4) . . . . ?
C6 C7 C8 C9 -0.6(6) . . . . ?
C7 C8 C9 C10 -0.1(6) . . . . ?
C8 C9 C10 C15 0.8(6) . . . . ?
C8 C9 C10 C11 -179.5(4) . . . . ?
C9 C10 C11 C12 -178.7(4) . . . . ?
C15 C10 C11 C12 1.0(5) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C14 -0.9(5) . . . . ?
C11 C12 C13 C16 178.8(3) . . . . ?
C16 C13 C14 C3 1.4(5) . . . . ?
C12 C13 C14 C3 -179.0(3) . . . . ?
C16 C13 C14 C15 -178.3(3) . . . . ?
C12 C13 C14 C15 1.4(5) . . . . ?
C2 C3 C14 C13 0.4(5) . . . . ?
C4 C3 C14 C13 180.0(3) . . . . ?
C2 C3 C14 C15 -179.9(3) . . . . ?
C4 C3 C14 C15 -0.3(5) . . . . ?
C7 C6 C15 C10 0.1(5) . . . . ?
C5 C6 C15 C10 -179.0(3) . . . . ?
C7 C6 C15 C14 -179.9(3) . . . . ?
C5 C6 C15 C14 1.0(5) . . . . ?
C9 C10 C15 C6 -0.8(5) . . . . ?
C11 C10 C15 C6 179.5(3) . . . . ?
C9 C10 C15 C14 179.2(3) . . . . ?
C11 C10 C15 C14 -0.4(5) . . . . ?
C13 C14 C15 C6 179.3(3) . . . . ?
C3 C14 C15 C6 -0.4(5) . . . . ?
C13 C14 C15 C10 -0.7(5) . . . . ?
C3 C14 C15 C10 179.6(3) . . . . ?
C2 C1 C16 C13 1.5(6) . . . . ?
C2 C1 C16 C17 -176.7(3) . . . . ?
C14 C13 C16 C1 -2.3(5) . . . . ?
C12 C13 C16 C1 178.1(3) . . . . ?
C14 C13 C16 C17 175.9(3) . . . . ?
C12 C13 C16 C17 -3.8(5) . . . . ?
C1 C16 C17 C18 -1.6(6) . . . . ?
C13 C16 C17 C18 -179.7(4) . . . . ?
C16 C17 C18 C19 177.9(4) . . . . ?
C17 C18 C19 O1 -6.9(6) . . . . ?
C17 C18 C19 C20 172.9(4) . . . . ?
O1 C19 C20 C25 172.1(4) . . . . ?
C18 C19 C20 C25 -7.7(6) . . . . ?
O1 C19 C20 C21 -5.4(6) . . . . ?
C18 C19 C20 C21 174.8(3) . . . . ?
C25 C20 C21 C22 -0.3(5) . . . . ?
C19 C20 C21 C22 177.3(3) . . . . ?
C20 C21 C22 F1 179.3(3) . . . . ?
C20 C21 C22 C23 0.3(6) . . . . ?
C26 O2 C23 C24 -2.8(6) . . . . ?
C26 O2 C23 C22 178.4(4) . . . . ?
F1 C22 C23 O2 -0.5(5) . . . . ?
C21 C22 C23 O2 178.6(3) . . . . ?
F1 C22 C23 C24 -179.4(3) . . . . ?
C21 C22 C23 C24 -0.3(6) . . . . ?
O2 C23 C24 C25 -178.4(4) . . . . ?
C22 C23 C24 C25 0.4(6) . . . . ?
C23 C24 C25 C20 -0.4(6) . . . . ?
C21 C20 C25 C24 0.3(6) . . . . ?
C19 C20 C25 C24 -177.2(3) . . . . ?
