#------------------------------------------------------------------------------
#$Date: 2021-09-06 13:34:05 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268695 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/25/7242540.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_7242540
loop_
_publ_author_name
'Shu, Yuanhong'
'Ye, Kaiqi'
'Yue, Yuan'
'Sun, Jingbo'
'Wang, Haoran'
'Zhong, Jiangbin'
'Yang, Xiqiao'
'Gao, Hongqiang'
'Lu, Ran'
_publ_section_title
;
 Fluorine as a robust balancer for tuning the reactivity of
 topo-photoreactions of chalcones and the photomechanical effects of
 molecular crystals
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              5856
_journal_page_last               5868
_journal_paper_doi               10.1039/D1CE00086A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C15 H9 F3 O'
_chemical_formula_sum            'C15 H9 F3 O'
_chemical_formula_weight         262.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc248st1
_audit_creation_date             2018-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2021-03-11 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.147(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9052(11)
_cell_length_b                   3.7985(3)
_cell_length_c                   23.3553(18)
_cell_measurement_reflns_used    4831
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.453
_cell_measurement_theta_min      2.646
_cell_volume                     1190.74(16)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.965
_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  0.0834
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15515
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.646
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.211
_refine_ls_R_factor_all          0.1904
_refine_ls_R_factor_gt           0.1028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0333P)²+2.2257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1856
_refine_ls_wR_factor_ref         0.2145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1342
_reflns_number_total             2633
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00086a31.cif
_cod_data_source_block           2FChF-4
_cod_depositor_comments
'Adding full bibliography for 7242537--7242549.cif.'
_cod_database_code               7242540
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C9(H9), C11(H11), C13(H13), C14(H14), C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 1.0505(2) 0.8417(10) 0.67776(14) 0.0897(11) Uani 1 1 d . . . . .
F2 F 0.3477(2) 0.5555(11) 0.74929(13) 0.0961(12) Uani 1 1 d . . . . .
F3 F 0.1470(2) 0.1253(11) 0.57067(14) 0.1002(13) Uani 1 1 d . . . . .
O4 O 0.6430(2) 0.2345(11) 0.53082(15) 0.0727(11) Uani 1 1 d . . . . .
C1 C 0.9555(3) 0.7295(14) 0.6540(2) 0.0585(13) Uani 1 1 d . . . . .
C2 C 0.9305(3) 0.6008(14) 0.5979(2) 0.0607(14) Uani 1 1 d . . . . .
H2 H 0.9772 0.5901 0.5758 0.073 Uiso 1 1 calc R . . . .
C3 C 0.8344(3) 0.4864(13) 0.5743(2) 0.0530(12) Uani 1 1 d . . . . .
H3 H 0.8161 0.3958 0.5360 0.064 Uiso 1 1 calc R . . . .
C4 C 0.7647(3) 0.5049(12) 0.60723(18) 0.0443(11) Uani 1 1 d . . . . .
C5 C 0.6622(3) 0.3714(14) 0.5792(2) 0.0516(12) Uani 1 1 d . . . . .
C6 C 0.5848(3) 0.4165(15) 0.6112(2) 0.0628(15) Uani 1 1 d . . . . .
H6 H 0.5999 0.5304 0.6477 0.075 Uiso 1 1 calc R . . . .
C7 C 0.4923(3) 0.2929(15) 0.5876(2) 0.0621(14) Uani 1 1 d . . . . .
H7 H 0.4808 0.1817 0.5509 0.075 Uiso 1 1 calc R . . . .
C8 C 0.4086(3) 0.3169(13) 0.61397(19) 0.0489(12) Uani 1 1 d . . . . .
C9 C 0.3158(3) 0.2106(13) 0.5802(2) 0.0531(12) Uani 1 1 d . . . . .
H9 H 0.3075 0.1283 0.5417 0.064 Uiso 1 1 calc R . . . .
C10 C 0.2375(3) 0.2287(14) 0.6043(2) 0.0603(14) Uani 1 1 d . . . . .
C11 C 0.2451(4) 0.3423(15) 0.6605(2) 0.0682(15) Uani 1 1 d . . . . .
H11 H 0.1902 0.3503 0.6762 0.082 Uiso 1 1 calc R . . . .
C12 C 0.3375(4) 0.4439(14) 0.6926(2) 0.0586(13) Uani 1 1 d . . . . .
C13 C 0.4190(3) 0.4373(13) 0.67150(19) 0.0533(12) Uani 1 1 d . . . . .
H13 H 0.4806 0.5114 0.6948 0.064 Uiso 1 1 calc R . . . .
C14 C 0.7940(3) 0.6394(13) 0.6638(2) 0.0547(13) Uani 1 1 d . . . . .
H14 H 0.7478 0.6541 0.6862 0.066 Uiso 1 1 calc R . . . .
C15 C 0.8901(3) 0.7529(14) 0.6880(2) 0.0607(13) Uani 1 1 d . . . . .
H15 H 0.9096 0.8426 0.7264 0.073 Uiso 1 1 calc R . . . .
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
C2 C1 F1 118.9(4) . . ?
C2 C1 C15 123.2(4) . . ?
C15 C1 F1 117.9(5) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.5(4) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 117.8(4) . . ?
C14 C4 C3 118.5(4) . . ?
C14 C4 C5 123.8(4) . . ?
O4 C5 C4 120.5(4) . . ?
O4 C5 C6 120.8(4) . . ?
C6 C5 C4 118.6(4) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 119.9(5) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 116.9 . . ?
C6 C7 C8 126.1(5) . . ?
C8 C7 H7 116.9 . . ?
C9 C8 C7 118.0(4) . . ?
C9 C8 C13 119.5(4) . . ?
C13 C8 C7 122.5(4) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.7(4) . . ?
C10 C9 H9 120.6 . . ?
F3 C10 C11 118.5(4) . . ?
C9 C10 F3 118.2(5) . . ?
C9 C10 C11 123.4(4) . . ?
C10 C11 H11 121.8 . . ?
C10 C11 C12 116.5(4) . . ?
C12 C11 H11 121.8 . . ?
F2 C12 C11 117.8(4) . . ?
C13 C12 F2 118.4(4) . . ?
C13 C12 C11 123.7(5) . . ?
C8 C13 H13 120.9 . . ?
C12 C13 C8 118.3(4) . . ?
C12 C13 H13 120.9 . . ?
C4 C14 H14 119.3 . . ?
C4 C14 C15 121.5(4) . . ?
C15 C14 H14 119.3 . . ?
C1 C15 C14 117.8(5) . . ?
C1 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
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 C1 1.361(5) . ?
F2 C12 1.363(5) . ?
F3 C10 1.356(5) . ?
O4 C5 1.209(5) . ?
C1 C2 1.356(7) . ?
C1 C15 1.357(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(5) . ?
C4 C5 1.493(6) . ?
C4 C14 1.375(6) . ?
C5 C6 1.471(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.345(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.455(6) . ?
C8 C9 1.386(6) . ?
C8 C13 1.391(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.351(6) . ?
C10 C11 1.359(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.363(6) . ?
C12 C13 1.349(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.378(6) . ?
C15 H15 0.9300 . ?
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
F1 C1 C2 C3 179.7(4) . . . . ?
F1 C1 C15 C14 179.9(4) . . . . ?
F2 C12 C13 C8 178.8(5) . . . . ?
F3 C10 C11 C12 -180.0(5) . . . . ?
O4 C5 C6 C7 2.5(8) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C2 C1 C15 C14 0.0(8) . . . . ?
C2 C3 C4 C5 -179.2(4) . . . . ?
C2 C3 C4 C14 -0.1(7) . . . . ?
C3 C4 C5 O4 4.0(7) . . . . ?
C3 C4 C5 C6 -174.8(4) . . . . ?
C3 C4 C14 C15 -0.3(7) . . . . ?
C4 C5 C6 C7 -178.7(5) . . . . ?
C4 C14 C15 C1 0.3(8) . . . . ?
C5 C4 C14 C15 178.7(5) . . . . ?
C5 C6 C7 C8 179.8(5) . . . . ?
C6 C7 C8 C9 172.8(5) . . . . ?
C6 C7 C8 C13 -8.1(9) . . . . ?
C7 C8 C9 C10 179.5(5) . . . . ?
C7 C8 C13 C12 -178.7(5) . . . . ?
C8 C9 C10 F3 179.7(5) . . . . ?
C8 C9 C10 C11 -0.8(8) . . . . ?
C9 C8 C13 C12 0.4(7) . . . . ?
C9 C10 C11 C12 0.6(9) . . . . ?
C10 C11 C12 F2 -179.3(5) . . . . ?
C10 C11 C12 C13 0.2(9) . . . . ?
C11 C12 C13 C8 -0.7(8) . . . . ?
C13 C8 C9 C10 0.3(7) . . . . ?
C14 C4 C5 O4 -175.0(5) . . . . ?
C14 C4 C5 C6 6.2(7) . . . . ?
C15 C1 C2 C3 -0.4(8) . . . . ?
