#------------------------------------------------------------------------------
#$Date: 2021-11-19 01:13:10 +0200 (Fri, 19 Nov 2021) $
#$Revision: 270749 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565321.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_1565321
loop_
_publ_author_name
'Wei, Xiao'
'Li, Bao'
'Yang, Zhiqiang'
'Zhong, RongLin'
'Wang, Yufei'
'Chen, yanan'
'Ding, Zeyang'
'Men, Guangwen'
'Yang, Zairan'
'Zhang, Houyu'
'Yang, Bing'
'Xu, Weiqing'
'Jiang, Shimei'
_publ_section_title
;
 Programmable photoresponsive materials based on a single molecule via
 distinct topochemical reactions
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04053G
_journal_year                    2021
_chemical_formula_moiety         'C21 H11 F6 N'
_chemical_formula_sum            'C21 H11 F6 N'
_chemical_formula_weight         391.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-10-01 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.315(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4375(3)
_cell_length_b                   15.1706(7)
_cell_length_c                   13.3563(6)
_cell_measurement_reflns_used    7751
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.69
_cell_volume                     1699.26(13)
_computing_cell_refinement       'Bruker D8 Venture'
_computing_data_collection       'Bruker D8 Venture'
_computing_data_reduction        'Bruker D8 Venture'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25701
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_min         2.685
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2014'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0685
_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)+(0.1013P)²+1.5234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1792
_refine_ls_wR_factor_ref         0.2209
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2547
_reflns_number_total             3894
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04053g4.cif
_cod_data_source_block           1_CCDC2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1565321
_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   0.985
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.4070(4) 1.31405(18) 0.3237(2) 0.0503(7) Uani 1 1 d . . . . .
H1 H 0.3596 1.3580 0.3587 0.060 Uiso 1 1 calc R U . . .
C2 C 0.4989(4) 1.3366(2) 0.2513(2) 0.0566(8) Uani 1 1 d . . . . .
H2 H 0.5141 1.3958 0.2370 0.068 Uiso 1 1 calc R U . . .
C3 C 0.5720(4) 1.2712(2) 0.1972(2) 0.0609(8) Uani 1 1 d . . . . .
H3 H 0.6363 1.2873 0.1480 0.073 Uiso 1 1 calc R U . . .
C4 C 0.5484(4) 1.1842(2) 0.2171(2) 0.0545(7) Uani 1 1 d . . . . .
H4 H 0.5957 1.1413 0.1805 0.065 Uiso 1 1 calc R U . . .
C5 C 0.4535(3) 1.15875(17) 0.29216(19) 0.0421(6) Uani 1 1 d . . . . .
C6 C 0.3815(3) 1.22501(17) 0.3473(2) 0.0427(6) Uani 1 1 d . . . . .
C7 C 0.2889(3) 1.19759(17) 0.4239(2) 0.0494(7) Uani 1 1 d . . . . .
H7 H 0.2411 1.2404 0.4604 0.059 Uiso 1 1 calc R U . . .
C8 C 0.2670(3) 1.11161(18) 0.4461(2) 0.0488(7) Uani 1 1 d . . . . .
H8 H 0.2063 1.0965 0.4976 0.059 Uiso 1 1 calc R U . . .
C9 C 0.3368(3) 1.04408(17) 0.3908(2) 0.0439(6) Uani 1 1 d . . . . .
C10 C 0.4263(3) 1.06947(17) 0.3157(2) 0.0462(6) Uani 1 1 d . . . . .
H10 H 0.4711 1.0259 0.2787 0.055 Uiso 1 1 calc R U . . .
C11 C 0.3218(3) 0.94966(16) 0.4081(2) 0.0432(6) Uani 1 1 d . . . . .
H11 H 0.3617 0.9149 0.3593 0.052 Uiso 1 1 calc R U . . .
C12 C 0.2613(3) 0.90270(16) 0.48101(19) 0.0388(5) Uani 1 1 d . . . . .
C13 C 0.2631(3) 0.80493(15) 0.48449(18) 0.0371(5) Uani 1 1 d . . . . .
C14 C 0.1715(3) 0.75873(16) 0.54753(19) 0.0405(6) Uani 1 1 d . . . . .
H14 H 0.1088 0.7896 0.5887 0.049 Uiso 1 1 calc R U . . .
C15 C 0.1725(3) 0.66748(17) 0.5498(2) 0.0424(6) Uani 1 1 d . . . . .
C16 C 0.2655(3) 0.62003(17) 0.48995(19) 0.0431(6) Uani 1 1 d . . . . .
H16 H 0.2655 0.5587 0.4913 0.052 Uiso 1 1 calc R U . . .
C17 C 0.3584(3) 0.66525(16) 0.42812(19) 0.0406(6) Uani 1 1 d . . . . .
C18 C 0.3577(3) 0.75603(16) 0.42481(19) 0.0393(6) Uani 1 1 d . . . . .
H18 H 0.4208 0.7852 0.3825 0.047 Uiso 1 1 calc R U . . .
C19 C 0.1922(4) 0.94525(17) 0.5612(2) 0.0486(7) Uani 1 1 d . . . . .
C20 C 0.0708(4) 0.6185(2) 0.6149(3) 0.0579(8) Uani 1 1 d . . . . .
C21 C 0.4678(4) 0.61555(18) 0.3677(2) 0.0536(7) Uani 1 1 d . . . . .
F1 F -0.0685(4) 0.5956(2) 0.5641(2) 0.0995(11) Uani 0.938(6) 1 d . . P A 1
F2 F 0.1366(4) 0.54433(19) 0.6487(3) 0.1177(15) Uani 0.938(6) 1 d . . P A 1
F3 F 0.0329(4) 0.66410(17) 0.6918(2) 0.0965(12) Uani 0.938(6) 1 d . . P A 1
F1' F 0.015(5) 0.546(3) 0.585(3) 0.068(11) Uiso 0.062(6) 1 d . . P A 2
F2' F 0.140(4) 0.601(3) 0.706(3) 0.068(11) Uiso 0.062(6) 1 d . . P A 2
F3' F -0.061(7) 0.646(4) 0.625(5) 0.110(17) Uiso 0.062(6) 1 d . . P A 2
F4 F 0.4158(4) 0.53574(17) 0.3431(3) 0.1050(13) Uani 0.934(5) 1 d . . P B 1
F5 F 0.4912(4) 0.65376(17) 0.2832(2) 0.1001(13) Uani 0.934(5) 1 d . . P B 1
F6 F 0.6097(3) 0.6040(2) 0.4184(2) 0.1080(13) Uani 0.934(5) 1 d . . P B 1
F4' F 0.512(3) 0.5437(18) 0.409(2) 0.049(8) Uiso 0.066(5) 1 d . . P B 2
F5' F 0.411(4) 0.589(3) 0.290(3) 0.082(12) Uiso 0.066(5) 1 d . . P B 2
F6' F 0.591(4) 0.663(2) 0.353(3) 0.063(9) Uiso 0.066(5) 1 d . . P B 2
N1 N 0.1362(4) 0.97658(19) 0.6256(2) 0.0810(10) Uani 1 1 d . . . . .
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'
N N 0.0061 0.0033 '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 C6 121.2(3) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C10 122.7(2) . . ?
C4 C5 C6 119.0(2) . . ?
C10 C5 C6 118.2(2) . . ?
C1 C6 C7 123.6(3) . . ?
C1 C6 C5 118.6(3) . . ?
C7 C6 C5 117.9(2) . . ?
C8 C7 C6 122.7(2) . . ?
C8 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C7 C8 C9 120.2(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 117.9(2) . . ?
C10 C9 C11 117.1(2) . . ?
C8 C9 C11 125.1(2) . . ?
C9 C10 C5 123.1(2) . . ?
C9 C10 H10 118.5 . . ?
C5 C10 H10 118.5 . . ?
C12 C11 C9 132.7(2) . . ?
C12 C11 H11 113.6 . . ?
C9 C11 H11 113.6 . . ?
C11 C12 C19 121.3(2) . . ?
C11 C12 C13 123.1(2) . . ?
C19 C12 C13 115.6(2) . . ?
C14 C13 C18 117.8(2) . . ?
C14 C13 C12 121.2(2) . . ?
C18 C13 C12 121.1(2) . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 C20 118.6(2) . . ?
C14 C15 C20 120.7(2) . . ?
C17 C16 C15 118.9(2) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 C21 119.2(2) . . ?
C16 C17 C21 119.8(2) . . ?
C17 C18 C13 120.8(2) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
N1 C19 C12 178.0(3) . . ?
F3' C20 F1' 91(3) . . ?
F3 C20 F2 108.3(3) . . ?
F3' C20 F2' 107(3) . . ?
F1' C20 F2' 104(2) . . ?
F3 C20 F1 105.0(3) . . ?
F2 C20 F1 105.5(3) . . ?
F3' C20 C15 119(2) . . ?
F1' C20 C15 118.3(16) . . ?
F3 C20 C15 113.7(3) . . ?
F2 C20 C15 112.4(3) . . ?
F2' C20 C15 114.5(15) . . ?
F1 C20 C15 111.5(3) . . ?
F5' C21 F4' 99(2) . . ?
F5' C21 F6' 108(3) . . ?
F4' C21 F6' 110(2) . . ?
F5 C21 F4 105.7(3) . . ?
F5 C21 F6 106.8(3) . . ?
F4 C21 F6 105.3(3) . . ?
F5' C21 C17 115.9(19) . . ?
F4' C21 C17 112.0(12) . . ?
F6' C21 C17 111.1(13) . . ?
F5 C21 C17 113.9(2) . . ?
F4 C21 C17 112.9(3) . . ?
F6 C21 C17 111.6(3) . . ?
C20 F1' F3' 43(2) . . ?
C20 F3' F1' 45(2) . . ?
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
C1 C2 1.348(4) . ?
C1 C6 1.409(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.409(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(4) . ?
C4 H4 0.9300 . ?
C5 C10 1.415(4) . ?
C5 C6 1.421(4) . ?
C6 C7 1.417(4) . ?
C7 C8 1.355(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.428(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(4) . ?
C9 C11 1.459(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.351(4) . ?
C11 H11 0.9300 . ?
C12 C19 1.428(4) . ?
C12 C13 1.484(3) . ?
C13 C14 1.393(3) . ?
C13 C18 1.401(3) . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(4) . ?
C15 C20 1.486(4) . ?
C16 C17 1.382(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(3) . ?
C17 C21 1.495(4) . ?
C18 H18 0.9300 . ?
C19 N1 1.131(4) . ?
C20 F3' 1.21(6) . ?
C20 F1' 1.25(4) . ?
C20 F3 1.308(4) . ?
C20 F2 1.313(4) . ?
C20 F2' 1.31(3) . ?
C20 F1 1.336(5) . ?
C21 F5' 1.17(4) . ?
C21 F4' 1.26(3) . ?
C21 F6' 1.30(3) . ?
C21 F5 1.303(4) . ?
C21 F4 1.317(4) . ?
C21 F6 1.321(4) . ?
F1' F3' 1.76(7) . ?
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
C6 C1 C2 C3 0.0(5) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C10 -179.7(3) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C2 C1 C6 C7 178.7(3) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C10 C5 C6 C1 -179.5(3) . . . . ?
C4 C5 C6 C7 -178.8(3) . . . . ?
C10 C5 C6 C7 1.1(4) . . . . ?
C1 C6 C7 C8 -179.3(3) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
C6 C7 C8 C9 -0.8(5) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C7 C8 C9 C11 179.9(3) . . . . ?
C8 C9 C10 C5 0.8(4) . . . . ?
C11 C9 C10 C5 -178.7(3) . . . . ?
C4 C5 C10 C9 178.3(3) . . . . ?
C6 C5 C10 C9 -1.6(4) . . . . ?
C10 C9 C11 C12 170.8(3) . . . . ?
C8 C9 C11 C12 -8.7(5) . . . . ?
C9 C11 C12 C19 1.1(5) . . . . ?
C9 C11 C12 C13 -178.2(3) . . . . ?
C11 C12 C13 C14 -166.5(3) . . . . ?
C19 C12 C13 C14 14.2(4) . . . . ?
C11 C12 C13 C18 13.8(4) . . . . ?
C19 C12 C13 C18 -165.5(2) . . . . ?
C18 C13 C14 C15 -0.9(4) . . . . ?
C12 C13 C14 C15 179.4(2) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C13 C14 C15 C20 -178.1(3) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C20 C15 C16 C17 179.0(3) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C15 C16 C17 C21 176.1(3) . . . . ?
C16 C17 C18 C13 0.3(4) . . . . ?
C21 C17 C18 C13 -176.6(2) . . . . ?
C14 C13 C18 C17 0.6(4) . . . . ?
C12 C13 C18 C17 -179.8(2) . . . . ?
C16 C15 C20 F3' -141(4) . . . . ?
C14 C15 C20 F3' 37(4) . . . . ?
C16 C15 C20 F1' -32(2) . . . . ?
C14 C15 C20 F1' 147(2) . . . . ?
C16 C15 C20 F3 157.2(3) . . . . ?
C14 C15 C20 F3 -24.2(5) . . . . ?
C16 C15 C20 F2 33.8(5) . . . . ?
C14 C15 C20 F2 -147.6(3) . . . . ?
C16 C15 C20 F2' 91(2) . . . . ?
C14 C15 C20 F2' -91(2) . . . . ?
C16 C15 C20 F1 -84.4(4) . . . . ?
C14 C15 C20 F1 94.2(4) . . . . ?
C18 C17 C21 F5' -98(3) . . . . ?
C16 C17 C21 F5' 85(3) . . . . ?
C18 C17 C21 F4' 149.5(16) . . . . ?
C16 C17 C21 F4' -27.4(16) . . . . ?
C18 C17 C21 F6' 26.2(17) . . . . ?
C16 C17 C21 F6' -150.7(17) . . . . ?
C18 C17 C21 F5 -33.1(4) . . . . ?
C16 C17 C21 F5 150.0(3) . . . . ?
C18 C17 C21 F4 -153.7(3) . . . . ?
C16 C17 C21 F4 29.4(4) . . . . ?
C18 C17 C21 F6 87.9(3) . . . . ?
C16 C17 C21 F6 -89.0(4) . . . . ?
F2' C20 F1' F3' 108(3) . . . . ?
C15 C20 F1' F3' -124(3) . . . . ?
F2' C20 F3' F1' -105(3) . . . . ?
C15 C20 F3' F1' 124(2) . . . . ?
