#------------------------------------------------------------------------------
#$Date: 2021-09-06 13:34:05 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268695 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/25/7242539.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_7242539
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         'C32 H22 F6 O2'
_chemical_formula_sum            'C32 H22 F6 O2'
_chemical_formula_weight         552.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc248sw3
_audit_creation_date             2021-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-11 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.0840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.6767(5)
_cell_length_b                   8.6874(3)
_cell_length_c                   11.3310(4)
_cell_measurement_reflns_used    9749
_cell_measurement_temperature    116(2)
_cell_measurement_theta_max      28.286
_cell_measurement_theta_min      2.816
_cell_volume                     1286.89(8)
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      116.06
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16546
_diffrn_reflns_point_group_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_min         2.815
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 2024 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.271
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5436
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.271
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0542
_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)+2.0837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.820
_reflns_Friedel_fraction_max     0.717
_reflns_number_gt                5238
_reflns_number_total             5436
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00086a31.cif
_cod_data_source_block           D-3FChMe-4
_cod_depositor_comments
'Adding full bibliography for 7242537--7242549.cif.'
_cod_database_code               7242539
_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_max   0.977
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C14(H14), C22(H22), C23(H23)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C15(H15), C16(H16), C20(H20), C21(H21), C24(H24), C25(H25),
 C26(H26), C28(H28), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, 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 0.3958(2) 1.1420(3) 0.4967(2) 0.0203(6) Uani 1 1 d . . . . .
F2 F 0.7496(2) -0.0592(3) 0.4003(2) 0.0225(6) Uani 1 1 d . . . . .
F3 F 0.6087(2) 0.0934(3) 0.2236(2) 0.0212(6) Uani 1 1 d . . . . .
F4 F 0.7863(2) 0.0211(3) 0.6403(2) 0.0188(6) Uani 1 1 d . . . . .
F5 F 0.2540(2) 1.1685(3) 0.2751(3) 0.0252(7) Uani 1 1 d . . . . .
F6 F 0.2317(2) 0.9411(4) 0.1057(2) 0.0305(7) Uani 1 1 d . . . . .
O1 O 0.3927(2) 0.5734(4) 0.6208(3) 0.0156(6) Uani 1 1 d . . . . .
O2 O 0.6959(2) 0.6077(4) 0.3734(3) 0.0161(6) Uani 1 1 d . . . . .
C1 C 0.7185(3) 0.1034(5) 0.5529(4) 0.0136(9) Uani 1 1 d . . . . .
C2 C 0.6898(3) 0.6192(4) 0.4781(4) 0.0113(8) Uani 1 1 d . . . . .
C3 C 0.5980(3) 0.3110(5) 0.4941(4) 0.0109(8) Uani 1 1 d . . . . .
C4 C 0.6283(3) 0.1409(5) 0.3424(4) 0.0145(9) Uani 1 1 d . . . . .
C5 C 0.7005(3) 0.0601(5) 0.4318(4) 0.0143(8) Uani 1 1 d . . . . .
C6 C 0.7814(3) 0.6426(5) 0.5867(4) 0.0112(8) Uani 1 1 d . . . . .
C7 C 0.3654(3) 0.5501(5) 0.5089(4) 0.0118(8) Uani 1 1 d . . . . .
C8 C 0.5773(3) 0.2657(5) 0.3703(4) 0.0116(8) Uani 1 1 d . . . . .
H8 H 0.5288 0.3203 0.3068 0.014 Uiso 1 1 calc R . . . .
C9 C 0.4909(3) 0.6270(4) 0.3889(3) 0.0086(8) Uani 1 1 d . . . . .
H9 H 0.5082 0.5895 0.3140 0.010 Uiso 1 1 calc R . . . .
C10 C 0.3855(3) 1.0263(5) 0.4143(4) 0.0139(8) Uani 1 1 d . . . . .
C11 C 0.6686(3) 0.2279(5) 0.5853(4) 0.0115(8) Uani 1 1 d . . . . .
H11 H 0.6825 0.2564 0.6696 0.014 Uiso 1 1 calc R . . . .
C12 C 0.4342(3) 0.7780(5) 0.3590(4) 0.0106(8) Uani 1 1 d . . . . .
C13 C 0.2596(3) 0.5874(4) 0.4325(4) 0.0113(8) Uani 1 1 d . . . . .
C14 C 0.5863(3) 0.6121(5) 0.5022(3) 0.0091(8) Uani 1 1 d . . . . .
H14 H 0.5832 0.6882 0.5672 0.011 Uiso 1 1 calc R . . . .
C15 C 0.4460(3) 0.8964(5) 0.4452(4) 0.0110(8) Uani 1 1 d . . . . .
H15 H 0.4950 0.8879 0.5241 0.013 Uiso 1 1 calc R . . . .
C16 C 0.7770(3) 0.6299(5) 0.7068(4) 0.0156(9) Uani 1 1 d . . . . .
H16 H 0.7151 0.5991 0.7217 0.019 Uiso 1 1 calc R . . . .
C17 C 0.3031(4) 0.9245(6) 0.2164(4) 0.0199(10) Uani 1 1 d . . . . .
C18 C 0.9524(4) 0.7120(6) 0.7869(4) 0.0203(10) Uani 1 1 d . . . . .
C19 C 0.3134(3) 1.0424(5) 0.3018(4) 0.0169(9) Uani 1 1 d . . . . .
C20 C 0.2199(3) 0.5393(5) 0.3092(4) 0.0134(8) Uani 1 1 d . . . . .
H20 H 0.2602 0.4772 0.2725 0.016 Uiso 1 1 calc R . . . .
C21 C 0.8737(3) 0.6870(5) 0.5658(4) 0.0142(8) Uani 1 1 d . . . . .
H21 H 0.8788 0.6920 0.4841 0.017 Uiso 1 1 calc R . . . .
C22 C 0.5466(3) 0.4491(4) 0.5309(4) 0.0094(8) Uani 1 1 d . . . . .
H22 H 0.5457 0.4418 0.6186 0.011 Uiso 1 1 calc R . . . .
C23 C 0.4392(3) 0.4908(5) 0.4428(4) 0.0104(8) Uani 1 1 d . . . . .
H23 H 0.4094 0.4086 0.3809 0.012 Uiso 1 1 calc R . . . .
C24 C 0.3626(3) 0.7945(5) 0.2421(4) 0.0143(9) Uani 1 1 d . . . . .
H24 H 0.3555 0.7165 0.1814 0.017 Uiso 1 1 calc R . . . .
C25 C 0.9576(3) 0.7235(6) 0.6659(4) 0.0199(10) Uani 1 1 d . . . . .
H25 H 1.0193 0.7568 0.6517 0.024 Uiso 1 1 calc R . . . .
C26 C 0.1988(4) 0.6797(6) 0.4836(4) 0.0187(9) Uani 1 1 d . . . . .
H26 H 0.2244 0.7132 0.5668 0.022 Uiso 1 1 calc R . . . .
C27 C 0.0620(4) 0.6747(6) 0.2916(4) 0.0204(10) Uani 1 1 d . . . . .
C28 C 0.8626(3) 0.6619(6) 0.8062(4) 0.0190(10) Uani 1 1 d . . . . .
H28 H 0.8591 0.6490 0.8881 0.023 Uiso 1 1 calc R . . . .
C29 C 0.1014(4) 0.7228(6) 0.4139(4) 0.0227(10) Uani 1 1 d . . . . .
H29 H 0.0610 0.7857 0.4499 0.027 Uiso 1 1 calc R . . . .
C30 C 0.1219(3) 0.5826(5) 0.2413(4) 0.0186(9) Uani 1 1 d . . . . .
H30 H 0.0954 0.5482 0.1584 0.022 Uiso 1 1 calc R . . . .
C31 C -0.0448(4) 0.7225(7) 0.2162(5) 0.0300(12) Uani 1 1 d . . . . .
H31A H -0.0836 0.7559 0.2718 0.045 Uiso 1 1 calc GR . . . .
H31B H -0.0795 0.6350 0.1668 0.045 Uiso 1 1 calc GR . . . .
H31C H -0.0402 0.8077 0.1613 0.045 Uiso 1 1 calc GR . . . .
C32 C 1.0446(4) 0.7532(7) 0.8947(5) 0.0307(12) Uani 1 1 d . . . . .
H32A H 1.0888 0.6627 0.9188 0.046 Uiso 1 1 calc GR . . . .
H32B H 1.0215 0.7869 0.9647 0.046 Uiso 1 1 calc GR . . . .
H32C H 1.0829 0.8365 0.8703 0.046 Uiso 1 1 calc GR . . . .
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'
F F 0.0171 0.0103 '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'
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
F4 C1 C5 118.1(4) . . ?
F4 C1 C11 120.5(4) . . ?
C5 C1 C11 121.4(4) . . ?
O2 C2 C6 122.2(4) . . ?
O2 C2 C14 120.4(4) . . ?
C6 C2 C14 117.3(3) . . ?
C8 C3 C22 121.7(4) . . ?
C11 C3 C8 119.3(4) . . ?
C11 C3 C22 119.0(4) . . ?
F3 C4 C5 117.6(4) . . ?
F3 C4 C8 120.2(4) . . ?
C8 C4 C5 122.3(4) . . ?
F2 C5 C1 121.4(4) . . ?
F2 C5 C4 120.3(4) . . ?
C1 C5 C4 118.3(4) . . ?
C16 C6 C2 122.2(4) . . ?
C16 C6 C21 119.2(4) . . ?
C21 C6 C2 118.6(4) . . ?
O1 C7 C13 120.9(4) . . ?
O1 C7 C23 121.5(4) . . ?
C13 C7 C23 117.5(4) . . ?
C3 C8 H8 120.5 . . ?
C4 C8 C3 119.0(4) . . ?
C4 C8 H8 120.5 . . ?
C12 C9 H9 109.1 . . ?
C12 C9 C14 120.8(3) . . ?
C12 C9 C23 118.3(3) . . ?
C14 C9 H9 109.1 . . ?
C14 C9 C23 88.9(3) . . ?
C23 C9 H9 109.1 . . ?
F1 C10 C15 120.0(4) . . ?
F1 C10 C19 117.8(4) . . ?
C19 C10 C15 122.1(4) . . ?
C1 C11 C3 119.8(4) . . ?
C1 C11 H11 120.1 . . ?
C3 C11 H11 120.1 . . ?
C15 C12 C9 122.5(4) . . ?
C15 C12 C24 119.4(4) . . ?
C24 C12 C9 118.0(4) . . ?
C20 C13 C7 122.7(4) . . ?
C26 C13 C7 118.7(4) . . ?
C26 C13 C20 118.6(4) . . ?
C2 C14 C9 116.8(3) . . ?
C2 C14 H14 110.4 . . ?
C2 C14 C22 117.8(3) . . ?
C9 C14 H14 110.4 . . ?
C9 C14 C22 89.4(3) . . ?
C22 C14 H14 110.4 . . ?
C10 C15 C12 119.2(4) . . ?
C10 C15 H15 120.4 . . ?
C12 C15 H15 120.4 . . ?
C6 C16 H16 119.7 . . ?
C6 C16 C28 120.7(4) . . ?
C28 C16 H16 119.7 . . ?
F6 C17 C19 117.7(4) . . ?
F6 C17 C24 120.4(4) . . ?
C24 C17 C19 121.8(4) . . ?
C25 C18 C32 120.2(4) . . ?
C28 C18 C25 118.8(4) . . ?
C28 C18 C32 120.9(4) . . ?
F5 C19 C10 120.9(4) . . ?
F5 C19 C17 120.9(4) . . ?
C10 C19 C17 118.1(4) . . ?
C13 C20 H20 120.0 . . ?
C30 C20 C13 120.0(4) . . ?
C30 C20 H20 120.0 . . ?
C6 C21 H21 120.3 . . ?
C25 C21 C6 119.5(4) . . ?
C25 C21 H21 120.3 . . ?
C3 C22 C14 116.0(3) . . ?
C3 C22 H22 111.5 . . ?
C3 C22 C23 115.8(3) . . ?
C14 C22 H22 111.5 . . ?
C23 C22 C14 88.6(3) . . ?
C23 C22 H22 111.5 . . ?
C7 C23 C9 112.0(3) . . ?
C7 C23 C22 113.8(3) . . ?
C7 C23 H23 113.4 . . ?
C9 C23 H23 113.4 . . ?
C22 C23 C9 88.6(3) . . ?
C22 C23 H23 113.4 . . ?
C12 C24 H24 120.3 . . ?
C17 C24 C12 119.3(4) . . ?
C17 C24 H24 120.3 . . ?
C18 C25 H25 119.5 . . ?
C21 C25 C18 121.0(4) . . ?
C21 C25 H25 119.5 . . ?
C13 C26 H26 119.7 . . ?
C29 C26 C13 120.6(4) . . ?
C29 C26 H26 119.7 . . ?
C29 C27 C31 120.3(5) . . ?
C30 C27 C29 118.7(4) . . ?
C30 C27 C31 121.0(4) . . ?
C16 C28 H28 119.7 . . ?
C18 C28 C16 120.7(4) . . ?
C18 C28 H28 119.7 . . ?
C26 C29 C27 120.7(4) . . ?
C26 C29 H29 119.6 . . ?
C27 C29 H29 119.6 . . ?
C20 C30 H30 119.3 . . ?
C27 C30 C20 121.4(4) . . ?
C27 C30 H30 119.3 . . ?
C27 C31 H31A 109.5 . . ?
C27 C31 H31B 109.5 . . ?
C27 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C18 C32 H32A 109.5 . . ?
C18 C32 H32B 109.5 . . ?
C18 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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 C10 1.351(5) . ?
F2 C5 1.339(5) . ?
F3 C4 1.357(5) . ?
F4 C1 1.346(5) . ?
F5 C19 1.344(5) . ?
F6 C17 1.352(5) . ?
O1 C7 1.228(5) . ?
O2 C2 1.218(5) . ?
C1 C5 1.374(6) . ?
C1 C11 1.385(6) . ?
C2 C6 1.489(6) . ?
C2 C14 1.519(6) . ?
C3 C8 1.404(6) . ?
C3 C11 1.392(6) . ?
C3 C22 1.510(5) . ?
C4 C5 1.381(6) . ?
C4 C8 1.375(6) . ?
C6 C16 1.385(6) . ?
C6 C21 1.405(6) . ?
C7 C13 1.488(6) . ?
C7 C23 1.513(6) . ?
C8 H8 0.9500 . ?
C9 H9 1.0000 . ?
C9 C12 1.512(5) . ?
C9 C14 1.543(5) . ?
C9 C23 1.590(5) . ?
C10 C15 1.382(6) . ?
C10 C19 1.371(6) . ?
C11 H11 0.9500 . ?
C12 C15 1.394(6) . ?
C12 C24 1.404(6) . ?
C13 C20 1.405(6) . ?
C13 C26 1.397(6) . ?
C14 H14 1.0000 . ?
C14 C22 1.584(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C28 1.393(6) . ?
C17 C19 1.387(7) . ?
C17 C24 1.372(6) . ?
C18 C25 1.397(7) . ?
C18 C28 1.380(7) . ?
C18 C32 1.518(6) . ?
C20 H20 0.9500 . ?
C20 C30 1.388(6) . ?
C21 H21 0.9500 . ?
C21 C25 1.393(6) . ?
C22 H22 1.0000 . ?
C22 C23 1.557(6) . ?
C23 H23 1.0000 . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C26 C29 1.385(7) . ?
C27 C29 1.396(7) . ?
C27 C30 1.382(7) . ?
C27 C31 1.517(6) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
