#------------------------------------------------------------------------------
#$Date: 2021-11-19 01:13:10 +0200 (Fri, 19 Nov 2021) $
#$Revision: 270749 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565322.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_1565322
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      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
;
2021-07-23 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                94.944(4)
_cell_angle_beta                 94.830(4)
_cell_angle_gamma                110.235(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8885(8)
_cell_length_b                   9.5215(10)
_cell_length_c                   12.4914(13)
_cell_measurement_reflns_used    8360
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.90
_cell_volume                     870.50(16)
_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      99(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0361
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26410
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         2.904
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2014'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.015(4)
_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   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0536
_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)+(0.0531P)²+0.3774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1554
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2510
_reflns_number_total             3988
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04053g4.cif
_cod_data_source_block           mo_WX0919_2_0m
_cod_database_code               1565322
_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   0.983
_shelx_estimated_absorpt_t_max   0.987
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
C6 C -0.01093(18) -0.13499(14) -0.22985(10) 0.0514(5) Uani 0.942(2) 1 d G . P A
1
C1 C -0.0965(2) -0.28399(15) -0.21234(10) 0.0538(5) Uani 0.942(2) 1 d G . P A 1
C2 C -0.2183(2) -0.38665(13) -0.29396(13) 0.0662(7) Uani 0.942(2) 1 d G . P A 1
H2 H -0.2768 -0.4885 -0.2820 0.079 Uiso 0.942(2) 1 calc R U P A 1
C3 C -0.2546(2) -0.34030(18) -0.39310(11) 0.0738(7) Uani 0.942(2) 1 d G . P A 1
H3 H -0.3379 -0.4105 -0.4489 0.089 Uiso 0.942(2) 1 calc R U P A 1
C4 C -0.1690(2) -0.1913(2) -0.41062(10) 0.0767(8) Uani 0.942(2) 1 d G . P A 1
H4 H -0.1938 -0.1596 -0.4784 0.092 Uiso 0.942(2) 1 calc R U P A 1
C5 C -0.0472(2) -0.08865(15) -0.32899(12) 0.0686(7) Uani 0.942(2) 1 d G . P A 1
H5 H 0.0113 0.0132 -0.3410 0.082 Uiso 0.942(2) 1 calc R U P A 1
C7 C 0.1135(3) -0.0324(2) -0.14491(17) 0.0529(5) Uani 0.942(2) 1 d . . P A 1
H7 H 0.1712 0.0698 -0.1564 0.063 Uiso 0.942(2) 1 calc R U P A 1
C8 C 0.1527(3) -0.0766(2) -0.04666(17) 0.0509(5) Uani 0.942(2) 1 d . . P A 1
C9 C 0.0613(3) -0.2272(3) -0.02954(19) 0.0595(6) Uani 0.942(2) 1 d . . P A 1
H9 H 0.0840 -0.2591 0.0385 0.071 Uiso 0.942(2) 1 calc R U P A 1
C10 C -0.0595(3) -0.3278(3) -0.10940(19) 0.0619(6) Uani 0.942(2) 1 d . . P A 1
H10 H -0.1198 -0.4287 -0.0960 0.074 Uiso 0.942(2) 1 calc R U P A 1
C11 C 0.2822(3) 0.0392(2) 0.03535(17) 0.0559(5) Uani 1 1 d . . . . .
H11 H 0.2972 0.1404 0.0251 0.067 Uiso 0.942(2) 1 calc R U P A 1
H11A H 0.2895 0.1413 0.0449 0.067 Uiso 0.058(2) 1 calc R U P A 2
C12 C 0.3822(3) 0.0233(2) 0.12235(16) 0.0528(5) Uani 1 1 d . . . . .
C13 C 0.3779(3) -0.1237(3) 0.1442(2) 0.0692(6) Uani 1 1 d . . . . .
C14 C 0.5072(3) 0.1516(2) 0.19997(16) 0.0502(5) Uani 1 1 d . . . . .
C15 C 0.5763(3) 0.2966(2) 0.17053(17) 0.0564(5) Uani 1 1 d . . . . .
H15 H 0.5457 0.3143 0.0990 0.068 Uiso 1 1 calc R U . . .
C16 C 0.6892(3) 0.4149(2) 0.24492(18) 0.0573(5) Uani 1 1 d . . . . .
C17 C 0.7378(3) 0.3918(2) 0.34886(17) 0.0573(5) Uani 1 1 d . . . . .
H17 H 0.8162 0.4736 0.3993 0.069 Uiso 1 1 calc R U . . .
C18 C 0.6708(3) 0.2485(2) 0.37836(16) 0.0535(5) Uani 1 1 d . . . . .
C19 C 0.5570(3) 0.1292(2) 0.30464(16) 0.0527(5) Uani 1 1 d . . . . .
H19 H 0.5125 0.0309 0.3260 0.063 Uiso 1 1 calc R U . . .
C20 C 0.7613(4) 0.5708(3) 0.2138(2) 0.0785(7) Uani 1 1 d . . . . .
C21 C 0.7137(3) 0.2240(3) 0.49220(19) 0.0682(6) Uani 1 1 d . . . . .
F1 F 0.6948(4) 0.5851(2) 0.11704(18) 0.1219(10) Uani 0.922(2) 1 d . . P B 1
F2 F 0.9408(3) 0.6240(2) 0.2182(2) 0.1232(9) Uani 0.922(2) 1 d . . P B 1
F3 F 0.7249(4) 0.6701(2) 0.28197(19) 0.1208(9) Uani 0.922(2) 1 d . . P B 1
F4 F 0.8710(2) 0.32208(19) 0.54009(13) 0.1045(6) Uani 1 1 d . . . . .
F5 F 0.5892(2) 0.2368(2) 0.55380(12) 0.1030(6) Uani 1 1 d . . . . .
F6 F 0.7189(3) 0.08823(18) 0.50083(13) 0.1044(6) Uani 1 1 d . . . . .
N1 N 0.3809(4) -0.2379(3) 0.1632(2) 0.1113(10) Uani 1 1 d . . . . .
C5A C -0.158(3) -0.4052(18) -0.1781(16) 0.060 Uiso 0.058(2) 1 d G U P A 2
H5A H -0.1496 -0.4600 -0.1190 0.072 Uiso 0.058(2) 1 calc R U P A 2
C4A C -0.273(3) -0.4776(18) -0.2722(18) 0.060 Uiso 0.058(2) 1 d G U P A 2
H4A H -0.3440 -0.5819 -0.2774 0.072 Uiso 0.058(2) 1 calc R U P A 2
C3A C -0.285(3) -0.397(2) -0.3586(16) 0.060 Uiso 0.058(2) 1 d G U P A 2
H3A H -0.3636 -0.4468 -0.4229 0.072 Uiso 0.058(2) 1 calc R U P A 2
C2A C -0.181(3) -0.245(2) -0.3509(13) 0.060 Uiso 0.058(2) 1 d G U P A 2
H2A H -0.1888 -0.1898 -0.4100 0.072 Uiso 0.058(2) 1 calc R U P A 2
C1A C -0.065(2) -0.1722(17) -0.2569(12) 0.060 Uiso 0.058(2) 1 d G U P A 2
C6A C -0.054(2) -0.2525(18) -0.1704(12) 0.060 Uiso 0.058(2) 1 d G U P A 2
C7A C 0.062(3) -0.180(2) -0.0764(13) 0.060 Uiso 0.058(2) 1 d G U P A 2
H7A H 0.0698 -0.2350 -0.0173 0.072 Uiso 0.058(2) 1 calc R U P A 2
C8A C 0.166(3) -0.027(2) -0.0687(16) 0.060 Uiso 0.058(2) 1 d G U P A 2
C9A C 0.154(3) 0.0528(19) -0.1551(19) 0.060 Uiso 0.058(2) 1 d G U P A 2
H9A H 0.2251 0.1571 -0.1499 0.072 Uiso 0.058(2) 1 calc R U P A 2
C10A C 0.039(3) -0.0196(18) -0.2492(16) 0.060 Uiso 0.058(2) 1 d G U P A 2
H10A H 0.0306 0.0353 -0.3083 0.072 Uiso 0.058(2) 1 calc R U P A 2
F1A F 0.859(3) 0.558(2) 0.1229(17) 0.080 Uiso 0.078(2) 1 d . U P B 2
F2A F 0.861(4) 0.663(2) 0.2816(18) 0.080 Uiso 0.078(2) 1 d . U P B 2
F3A F 0.632(3) 0.598(2) 0.177(2) 0.080 Uiso 0.078(2) 1 d . U P B 2
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
C1 C6 C5 120.0 . . ?
C1 C6 C7 118.81(13) . . ?
C5 C6 C7 121.20(13) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 C10 121.14(13) . . ?
C6 C1 C10 118.85(13) . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C8 C7 C6 122.00(18) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C9 118.34(19) . . ?
C7 C8 C11 117.3(2) . . ?
C9 C8 C11 124.3(2) . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C1 121.1(2) . . ?
C9 C10 H10 119.5 . . ?
C1 C10 H10 119.5 . . ?
C12 C11 C8 129.5(2) . . ?
C12 C11 C8A 149.2(10) . . ?
C12 C11 H11 115.2 . . ?
C8 C11 H11 115.2 . . ?
C12 C11 H11A 105.4 . . ?
C8A C11 H11A 105.4 . . ?
C11 C12 C13 120.66(19) . . ?
C11 C12 C14 123.8(2) . . ?
C13 C12 C14 115.47(19) . . ?
N1 C13 C12 177.5(3) . . ?
C19 C14 C15 118.34(18) . . ?
C19 C14 C12 120.31(18) . . ?
C15 C14 C12 121.35(18) . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 121.0(2) . . ?
C17 C16 C20 118.7(2) . . ?
C15 C16 C20 120.3(2) . . ?
C18 C17 C16 119.01(19) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 120.5(2) . . ?
C17 C18 C21 119.39(19) . . ?
C19 C18 C21 120.04(19) . . ?
C18 C19 C14 120.84(19) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
F2A C20 F3A 115.2(16) . . ?
F1 C20 F2 107.3(3) . . ?
F1 C20 F3 105.5(3) . . ?
F2 C20 F3 104.2(2) . . ?
F2A C20 F1A 108.8(15) . . ?
F3A C20 F1A 105.0(14) . . ?
F2A C20 C16 115.5(11) . . ?
F3A C20 C16 106.6(11) . . ?
F1 C20 C16 114.5(2) . . ?
F2 C20 C16 112.7(2) . . ?
F3 C20 C16 111.9(2) . . ?
F1A C20 C16 104.8(8) . . ?
F6 C21 F4 106.8(2) . . ?
F6 C21 F5 105.3(2) . . ?
F4 C21 F5 105.8(2) . . ?
F6 C21 C18 113.2(2) . . ?
F4 C21 C18 113.20(19) . . ?
F5 C21 C18 111.8(2) . . ?
C4A C5A C6A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C1A C2A C3A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C2A C1A C6A 120.0 . . ?
C2A C1A C10A 120.0 . . ?
C6A C1A C10A 120.0 . . ?
C7A C6A C1A 120.0 . . ?
C7A C6A C5A 120.0 . . ?
C1A C6A C5A 120.0 . . ?
C8A C7A C6A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C9A C8A C7A 120.0 . . ?
C9A C8A C11 124.2(13) . . ?
C7A C8A C11 115.7(13) . . ?
C8A C9A C10A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C9A C10A C1A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C1A C10A H10A 120.0 . . ?
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
C6 C1 1.3900 . ?
C6 C5 1.3900 . ?
C6 C7 1.424(2) . ?
C1 C2 1.3900 . ?
C1 C10 1.423(3) . ?
C2 C3 1.3900 . ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.408(3) . ?
C8 C11 1.470(3) . ?
C9 C10 1.366(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.339(3) . ?
C11 C8A 1.480(16) . ?
C11 H11 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C13 1.439(3) . ?
C12 C14 1.485(3) . ?
C13 N1 1.140(3) . ?
C14 C19 1.389(3) . ?
C14 C15 1.393(3) . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(3) . ?
C16 C20 1.494(3) . ?
C17 C18 1.378(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 C21 1.491(3) . ?
C19 H19 0.9500 . ?
C20 F2A 1.18(2) . ?
C20 F3A 1.20(2) . ?
C20 F1 1.314(3) . ?
C20 F2 1.323(3) . ?
C20 F3 1.338(4) . ?
C20 F1A 1.45(2) . ?
C21 F6 1.321(3) . ?
C21 F4 1.321(3) . ?
C21 F5 1.329(3) . ?
C5A C4A 1.3900 . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9500 . ?
C4A C3A 1.3900 . ?
C4A H4A 0.9500 . ?
C3A C2A 1.3900 . ?
C3A H3A 0.9500 . ?
C2A C1A 1.3900 . ?
C2A H2A 0.9500 . ?
C1A C6A 1.3900 . ?
C1A C10A 1.3900 . ?
C6A C7A 1.3900 . ?
C7A C8A 1.3900 . ?
C7A H7A 0.9500 . ?
C8A C9A 1.3900 . ?
C9A C10A 1.3900 . ?
C9A H9A 0.9500 . ?
C10A H10A 0.9500 . ?
