# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_SNA02_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2081858'
loop_
_audit_author_name
_audit_author_address
'Siti Nabilla Aliya Mohd Nizar'
;X ray Crystallography Unit, School of Physics, Universiti Sains Malaysia
Malaysia
;
_audit_update_record             
;
2021-05-05 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H17 F O2'
_chemical_formula_weight         380.39

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.506(4)
_cell_length_b                   9.968(5)
_cell_length_c                   12.308(6)
_cell_angle_alpha                97.824(8)
_cell_angle_beta                 102.058(7)
_cell_angle_gamma                98.891(7)
_cell_volume                     876.1(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1003
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      18.61

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.572
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20756
_diffrn_reflns_av_unetI/netI     0.0957
_diffrn_reflns_av_R_equivalents  0.0978
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.718
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3449
_reflns_number_gt                1512
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0792P)²+0.3509P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3449
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1670
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.2311
_refine_ls_wR_factor_gt          0.1646
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.045

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_kh03a_0m
_database_code_depnum_ccdc_archive 'CCDC 2164509'
loop_
_audit_author_name
_audit_author_address
'Siti Nabilla Aliya Mohd Nizar'
;X ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, USM, Penang
Malaysia
;
_audit_update_record             
;
2022-04-05 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H15 Br O'
_chemical_formula_weight         411.28

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   30.60(3)
_cell_length_b                   5.318(5)
_cell_length_c                   20.809(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.487(15)
_cell_angle_gamma                90
_cell_volume                     3383(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    568
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      13.71

_exptl_crystal_description       Plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.483
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.132
_exptl_absorpt_coefficient_mu    2.443
_shelx_estimated_absorpt_T_min   0.385
_shelx_estimated_absorpt_T_max   0.739
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39817
_diffrn_reflns_av_unetI/netI     0.1923
_diffrn_reflns_av_R_equivalents  0.4606
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.332
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2998
_reflns_number_gt                924
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0919P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2998
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2743
_refine_ls_R_factor_gt           0.0872
_refine_ls_wR_factor_ref         0.2499
_refine_ls_wR_factor_gt          0.1642
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Br1 Br -0.25683(4) -0.4260(3) -0.63505(7) 0.1213(8) Uani 1 1 d . . . . .
O1 O -0.4103(3) -0.0447(18) -0.8453(4) 0.111(3) Uani 1 1 d . . . . .
C1 C -0.5161(4) -0.752(3) -0.8376(6) 0.081(3) Uani 1 1 d . . . . .
H1A H -0.4941 -0.7802 -0.8062 0.098 Uiso 1 1 calc R U . . .
C2 C -0.5505(4) -0.910(2) -0.8409(6) 0.086(3) Uani 1 1 d . . . . .
H2A H -0.5522 -1.0440 -0.8122 0.103 Uiso 1 1 calc R U . . .
C3 C -0.5825(4) -0.871(2) -0.8866(6) 0.068(3) Uani 1 1 d . . . . .
C4 C -0.6197(5) -1.027(2) -0.8922(6) 0.090(4) Uani 1 1 d . . . . .
H4A H -0.6224 -1.1636 -0.8647 0.108 Uiso 1 1 calc R U . . .
C5 C -0.6510(4) -0.978(3) -0.9371(7) 0.095(4) Uani 1 1 d . . . . .
H5A H -0.6756 -1.0813 -0.9394 0.114 Uiso 1 1 calc R U . . .
C6 C -0.6486(5) -0.780(3) -0.9811(6) 0.083(4) Uani 1 1 d . . . . .
C7 C -0.6807(4) -0.748(3) -1.0267(7) 0.105(4) Uani 1 1 d . . . . .
H7A H -0.7055 -0.8498 -1.0290 0.126 Uiso 1 1 calc R U . . .
C8 C -0.6748(5) -0.562(3) -1.0681(7) 0.102(4) Uani 1 1 d . . . . .
H8A H -0.6960 -0.5401 -1.1010 0.122 Uiso 1 1 calc R U . . .
C9 C -0.6405(5) -0.403(2) -1.0661(6) 0.087(4) Uani 1 1 d . . . . .
H9A H -0.6393 -0.2697 -1.0950 0.104 Uiso 1 1 calc R U . . .
C10 C -0.6076(4) -0.441(3) -1.0208(6) 0.075(3) Uani 1 1 d . . . . .
C11 C -0.5703(4) -0.292(2) -1.0159(6) 0.083(3) Uani 1 1 d . . . . .
H11A H -0.5667 -0.1664 -1.0462 0.100 Uiso 1 1 calc R U . . .
C12 C -0.5405(4) -0.323(2) -0.9708(6) 0.076(3) Uani 1 1 d . . . . .
H12A H -0.5165 -0.2154 -0.9686 0.092 Uiso 1 1 calc R U . . .
C13 C -0.5435(4) -0.515(3) -0.9249(6) 0.074(3) Uani 1 1 d . . . . .
C14 C -0.5798(4) -0.675(3) -0.9298(6) 0.070(3) Uani 1 1 d . . . . .
C15 C -0.6120(4) -0.633(3) -0.9775(6) 0.071(3) Uani 1 1 d . . . . .
C16 C -0.5122(4) -0.557(3) -0.8775(6) 0.071(3) Uani 1 1 d . . . . .
C17 C -0.4762(4) -0.390(2) -0.8667(5) 0.081(3) Uani 1 1 d . . . . .
H17A H -0.4775 -0.2402 -0.8897 0.098 Uiso 1 1 calc R U . . .
C18 C -0.4427(4) -0.420(2) -0.8296(6) 0.084(3) Uani 1 1 d . . . . .
H18A H -0.4402 -0.5713 -0.8072 0.101 Uiso 1 1 calc R U . . .
C19 C -0.4086(4) -0.242(3) -0.8196(5) 0.075(3) Uani 1 1 d . . . . .
C20 C -0.3710(4) -0.296(3) -0.7771(6) 0.074(3) Uani 1 1 d . . . . .
C21 C -0.3687(4) -0.496(2) -0.7393(7) 0.089(4) Uani 1 1 d . . . . .
H21A H -0.3917 -0.6102 -0.7422 0.107 Uiso 1 1 calc R U . . .
C22 C -0.3356(5) -0.543(2) -0.6973(6) 0.089(4) Uani 1 1 d . . . . .
H22A H -0.3351 -0.6847 -0.6710 0.107 Uiso 1 1 calc R U . . .
C23 C -0.3031(4) -0.374(3) -0.6951(6) 0.082(4) Uani 1 1 d . . . . .
C24 C -0.3029(4) -0.175(3) -0.7324(7) 0.093(4) Uani 1 1 d . . . . .
H24A H -0.2795 -0.0632 -0.7303 0.112 Uiso 1 1 calc R U . . .
C25 C -0.3368(5) -0.136(2) -0.7730(6) 0.092(4) Uani 1 1 d . . . . .
H25A H -0.3370 0.0046 -0.7995 0.110 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Br1 C23 1.868(11) . ?
O1 C19 1.176(12) . ?
C1 C16 1.339(14) . ?
C1 C2 1.346(14) . ?
C1 H1A 0.9300 . ?
C2 C3 1.353(14) . ?
C2 H2A 0.9300 . ?
C3 C14 1.383(13) . ?
C3 C4 1.409(15) . ?
C4 C5 1.334(15) . ?
C4 H4A 0.9300 . ?
C5 C6 1.398(16) . ?
C5 H5A 0.9300 . ?
C6 C7 1.346(15) . ?
C6 C15 1.367(14) . ?
C7 C8 1.330(16) . ?
C7 H7A 0.9300 . ?
C8 C9 1.347(16) . ?
C8 H8A 0.9300 . ?
C9 C10 1.367(14) . ?
C9 H9A 0.9300 . ?
C10 C15 1.371(14) . ?
C10 C11 1.388(15) . ?
C11 C12 1.291(13) . ?
C11 H11A 0.9300 . ?
C12 C13 1.403(14) . ?
C12 H12A 0.9300 . ?
C13 C16 1.363(14) . ?
C13 C14 1.397(15) . ?
C14 C15 1.386(14) . ?
C16 C17 1.424(15) . ?
C17 C18 1.267(14) . ?
C17 H17A 0.9300 . ?
C18 C19 1.418(15) . ?
C18 H18A 0.9300 . ?
C19 C20 1.451(14) . ?
C20 C21 1.322(14) . ?
C20 C25 1.345(14) . ?
C21 C22 1.334(14) . ?
C21 H21A 0.9300 . ?
C22 C23 1.341(15) . ?
C22 H22A 0.9300 . ?
C23 C24 1.310(14) . ?
C24 C25 1.326(14) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?

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
C16 C1 C2 123.0(12) . . ?
C16 C1 H1A 118.5 . . ?
C2 C1 H1A 118.5 . . ?
C1 C2 C3 118.7(12) . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 H2A 120.7 . . ?
C2 C3 C14 120.7(12) . . ?
C2 C3 C4 121.6(14) . . ?
C14 C3 C4 117.6(12) . . ?
C5 C4 C3 119.7(12) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C6 123.3(13) . . ?
C4 C5 H5A 118.3 . . ?
C6 C5 H5A 118.3 . . ?
C7 C6 C15 122.5(15) . . ?
C7 C6 C5 120.0(16) . . ?
C15 C6 C5 117.4(15) . . ?
C8 C7 C6 115.8(15) . . ?
C8 C7 H7A 122.1 . . ?
C6 C7 H7A 122.1 . . ?
C7 C8 C9 125.1(13) . . ?
C7 C8 H8A 117.4 . . ?
C9 C8 H8A 117.4 . . ?
C8 C9 C10 118.5(13) . . ?
C8 C9 H9A 120.8 . . ?
C10 C9 H9A 120.8 . . ?
C9 C10 C15 118.3(13) . . ?
C9 C10 C11 122.9(15) . . ?
C15 C10 C11 118.7(12) . . ?
C12 C11 C10 122.2(12) . . ?
C12 C11 H11A 118.9 . . ?
C10 C11 H11A 118.9 . . ?
C11 C12 C13 121.4(12) . . ?
C11 C12 H12A 119.3 . . ?
C13 C12 H12A 119.3 . . ?
C16 C13 C14 119.0(13) . . ?
C16 C13 C12 123.1(14) . . ?
C14 C13 C12 117.9(12) . . ?
C3 C14 C15 121.6(14) . . ?
C3 C14 C13 118.8(12) . . ?
C15 C14 C13 119.6(14) . . ?
C6 C15 C10 119.6(13) . . ?
C6 C15 C14 120.3(16) . . ?
C10 C15 C14 120.1(13) . . ?
C1 C16 C13 119.8(12) . . ?
C1 C16 C17 118.3(12) . . ?
C13 C16 C17 121.8(14) . . ?
C18 C17 C16 128.2(13) . . ?
C18 C17 H17A 115.9 . . ?
C16 C17 H17A 115.9 . . ?
C17 C18 C19 125.1(13) . . ?
C17 C18 H18A 117.5 . . ?
C19 C18 H18A 117.5 . . ?
O1 C19 C18 120.8(12) . . ?
O1 C19 C20 118.1(13) . . ?
C18 C19 C20 121.0(13) . . ?
C21 C20 C25 116.7(11) . . ?
C21 C20 C19 122.8(14) . . ?
C25 C20 C19 120.5(14) . . ?
C20 C21 C22 124.1(12) . . ?
C20 C21 H21A 118.0 . . ?
C22 C21 H21A 118.0 . . ?
C21 C22 C23 115.8(12) . . ?
C21 C22 H22A 122.1 . . ?
C23 C22 H22A 122.1 . . ?
C24 C23 C22 123.0(12) . . ?
C24 C23 Br1 119.6(13) . . ?
C22 C23 Br1 117.4(13) . . ?
C23 C24 C25 118.6(12) . . ?
C23 C24 H24A 120.7 . . ?
C25 C24 H24A 120.7 . . ?
C24 C25 C20 121.8(12) . . ?
C24 C25 H25A 119.1 . . ?
C20 C25 H25A 119.1 . . ?

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(18) . . . . ?
C1 C2 C3 C14 0.9(16) . . . . ?
C1 C2 C3 C4 -179.1(11) . . . . ?
C2 C3 C4 C5 178.5(10) . . . . ?
C14 C3 C4 C5 -1.4(16) . . . . ?
C3 C4 C5 C6 1.5(18) . . . . ?
C4 C5 C6 C7 177.5(12) . . . . ?
C4 C5 C6 C15 0.8(18) . . . . ?
C15 C6 C7 C8 -0.5(19) . . . . ?
C5 C6 C7 C8 -177.1(12) . . . . ?
C6 C7 C8 C9 -2(2) . . . . ?
C7 C8 C9 C10 4(2) . . . . ?
C8 C9 C10 C15 -3.0(17) . . . . ?
C8 C9 C10 C11 178.2(11) . . . . ?
C9 C10 C11 C12 176.4(11) . . . . ?
C15 C10 C11 C12 -2.5(17) . . . . ?
C10 C11 C12 C13 2.0(18) . . . . ?
C11 C12 C13 C16 178.4(10) . . . . ?
C11 C12 C13 C14 0.4(16) . . . . ?
C2 C3 C14 C15 179.2(10) . . . . ?
C4 C3 C14 C15 -0.9(15) . . . . ?
C2 C3 C14 C13 -0.7(15) . . . . ?
C4 C3 C14 C13 179.3(9) . . . . ?
C16 C13 C14 C3 -0.6(15) . . . . ?
C12 C13 C14 C3 177.5(9) . . . . ?
C16 C13 C14 C15 179.6(9) . . . . ?
C12 C13 C14 C15 -2.4(15) . . . . ?
C7 C6 C15 C10 1.4(17) . . . . ?
C5 C6 C15 C10 178.1(10) . . . . ?
C7 C6 C15 C14 -179.8(11) . . . . ?
C5 C6 C15 C14 -3.1(16) . . . . ?
C9 C10 C15 C6 0.4(16) . . . . ?
C11 C10 C15 C6 179.3(10) . . . . ?
C9 C10 C15 C14 -178.4(10) . . . . ?
C11 C10 C15 C14 0.5(16) . . . . ?
C3 C14 C15 C6 3.2(15) . . . . ?
C13 C14 C15 C6 -176.9(10) . . . . ?
C3 C14 C15 C10 -178.0(10) . . . . ?
C13 C14 C15 C10 1.9(15) . . . . ?
C2 C1 C16 C13 -1.6(18) . . . . ?
C2 C1 C16 C17 175.2(11) . . . . ?
C14 C13 C16 C1 1.7(16) . . . . ?
C12 C13 C16 C1 -176.3(11) . . . . ?
C14 C13 C16 C17 -175.0(10) . . . . ?
C12 C13 C16 C17 7.0(16) . . . . ?
C1 C16 C17 C18 12.0(19) . . . . ?
C13 C16 C17 C18 -171.4(12) . . . . ?
C16 C17 C18 C19 -177.8(11) . . . . ?
C17 C18 C19 O1 2(2) . . . . ?
C17 C18 C19 C20 -178.8(11) . . . . ?
O1 C19 C20 C21 170.5(13) . . . . ?
C18 C19 C20 C21 -9.0(18) . . . . ?
O1 C19 C20 C25 -7.5(18) . . . . ?
C18 C19 C20 C25 173.1(11) . . . . ?
C25 C20 C21 C22 1.7(19) . . . . ?
C19 C20 C21 C22 -176.3(11) . . . . ?
C20 C21 C22 C23 -0.6(19) . . . . ?
C21 C22 C23 C24 -1.1(19) . . . . ?
C21 C22 C23 Br1 178.0(8) . . . . ?
C22 C23 C24 C25 1(2) . . . . ?
Br1 C23 C24 C25 -177.6(9) . . . . ?
C23 C24 C25 C20 0(2) . . . . ?
C21 C20 C25 C24 -1.3(19) . . . . ?
C19 C20 C25 C24 176.8(11) . . . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.069

