#------------------------------------------------------------------------------
#$Date: 2023-01-06 11:25:10 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280153 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/80/1568038.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_1568038
loop_
_publ_author_name
'Liu, Sen'
'Li, Jun'
'Hou, Tianjiao'
'Shen, Xuan'
_publ_section_title
;
 The study of a novel high selectivity pyrenyl-based fluorescence probe
 with aggregation-induced emission characteristics for Fe³⁺
 detection designed by a structure modulation strategy.
;
_journal_issue                   48
_journal_name_full
'Analytical methods : advancing methods and applications'
_journal_page_first              5081
_journal_page_last               5090
_journal_paper_doi               10.1039/d2ay01780f
_journal_volume                  14
_journal_year                    2022
_chemical_formula_moiety         'C22 H12 F3 N'
_chemical_formula_sum            'C22 H12 F3 N'
_chemical_formula_weight         347.33
_chemical_name_systematic        2-(pyren-1-yl)-5-(trifluoromethyl)pyridine
_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     dual
_audit_creation_date             2022-04-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-05-30 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.442(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.910(6)
_cell_length_b                   6.4608(15)
_cell_length_c                   9.318(2)
_cell_measurement_reflns_used    3112
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.561
_cell_measurement_theta_min      2.277
_cell_volume                     1615.2(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10777
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.518
_diffrn_source_current           25.0
_diffrn_source_power             1.125
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.236
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0566
_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)+(0.0685P)²+0.8201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1598
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2082
_reflns_number_total             2841
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ay01780f2.cif
_cod_data_source_block           14
_cod_depositor_comments
'Adding full bibliography for 1568038--1568039.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1568038
_shelx_shelxl_version_number     2018/3
_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   0.988
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C1(H1), C2(H2), C3(H3), C14(H14), C15(H15), C5(H5),
 C6(H6), C18(H18), C19(H19), C21(H21)
;
_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 0.43278(9) 1.1105(4) 0.0765(3) 0.1344(10) Uani 1 1 d . U . . .
F2 F 0.48219(8) 0.9744(5) 0.2314(3) 0.1375(11) Uani 1 1 d . . . . .
F3 F 0.46301(9) 0.8190(4) 0.0441(3) 0.1347(11) Uani 1 1 d . . . . .
N1 N 0.35503(7) 0.5361(3) 0.2564(2) 0.0494(6) Uani 1 1 d . . . . .
C12 C 0.16696(9) 0.1658(4) 0.5397(2) 0.0427(6) Uani 1 1 d . . . . .
H12 H 0.175197 0.046494 0.592155 0.051 Uiso 1 1 calc R U . . .
C11 C 0.11883(9) 0.2132(4) 0.5100(3) 0.0455(6) Uani 1 1 d . . . . .
H11 H 0.094454 0.126359 0.542138 0.055 Uiso 1 1 calc R U . . .
C10 C 0.10417(8) 0.3954(4) 0.4295(2) 0.0390(5) Uani 1 1 d . . . . .
C1 C 0.05447(9) 0.4505(4) 0.3979(3) 0.0521(7) Uani 1 1 d . . . . .
H1 H 0.029437 0.366302 0.429194 0.062 Uiso 1 1 calc R U . . .
C2 C 0.04171(9) 0.6279(5) 0.3210(3) 0.0602(8) Uani 1 1 d . . . . .
H2 H 0.008304 0.661604 0.300757 0.072 Uiso 1 1 calc R U . . .
C3 C 0.07816(9) 0.7552(4) 0.2739(3) 0.0525(7) Uani 1 1 d . . . . .
H3 H 0.069057 0.874519 0.222570 0.063 Uiso 1 1 calc R U . . .
C4 C 0.12850(8) 0.7078(4) 0.3022(2) 0.0376(5) Uani 1 1 d . . . . .
C9 C 0.14222(8) 0.5264(3) 0.3814(2) 0.0328(5) Uani 1 1 d . . . . .
C8 C 0.19335(8) 0.4748(3) 0.4114(2) 0.0319(5) Uani 1 1 d . . . . .
C13 C 0.20623(8) 0.2937(3) 0.4929(2) 0.0361(5) Uani 1 1 d . . . . .
C14 C 0.25620(9) 0.2470(4) 0.5237(3) 0.0436(6) Uani 1 1 d . . . . .
H14 H 0.265047 0.133333 0.581398 0.052 Uiso 1 1 calc R U . . .
C15 C 0.29298(9) 0.3664(4) 0.4701(3) 0.0427(6) Uani 1 1 d . . . . .
H15 H 0.326166 0.328739 0.489798 0.051 Uiso 1 1 calc R U . . .
C5 C 0.16758(9) 0.8324(4) 0.2516(2) 0.0408(6) Uani 1 1 d . . . . .
H5 H 0.159185 0.952658 0.200530 0.049 Uiso 1 1 calc R U . . .
C6 C 0.21575(8) 0.7817(3) 0.2754(2) 0.0384(5) Uani 1 1 d . . . . .
H6 H 0.239713 0.864422 0.237034 0.046 Uiso 1 1 calc R U . . .
C7 C 0.23146(8) 0.6018(3) 0.3593(2) 0.0327(5) Uani 1 1 d . . . . .
C16 C 0.28173(8) 0.5419(3) 0.3872(2) 0.0356(5) Uani 1 1 d . . . . .
C17 C 0.32394(8) 0.6549(4) 0.3268(2) 0.0389(5) Uani 1 1 d . . . . .
C18 C 0.33112(9) 0.8651(4) 0.3438(3) 0.0517(7) Uani 1 1 d . . . . .
H18 H 0.309511 0.942222 0.395796 0.062 Uiso 1 1 calc R U . . .
C19 C 0.37019(10) 0.9606(4) 0.2839(3) 0.0571(7) Uani 1 1 d . . . . .
H19 H 0.375113 1.102589 0.293396 0.069 Uiso 1 1 calc R U . . .
C20 C 0.40198(9) 0.8406(4) 0.2092(3) 0.0501(7) Uani 1 1 d . . . . .
C21 C 0.39324(9) 0.6314(4) 0.2001(3) 0.0546(7) Uani 1 1 d . . . . .
H21 H 0.415243 0.550827 0.151935 0.066 Uiso 1 1 calc R U . . .
C22 C 0.44463(11) 0.9366(6) 0.1428(4) 0.0714(9) 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'
N N 0.0061 0.0033 '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
C21 N1 C17 117.0(2) . . ?
C11 C12 H12 119.0 . . ?
C11 C12 C13 121.9(2) . . ?
C13 C12 H12 119.0 . . ?
C12 C11 H11 119.4 . . ?
C12 C11 C10 121.2(2) . . ?
C10 C11 H11 119.4 . . ?
C1 C10 C11 122.7(2) . . ?
C1 C10 C9 118.8(2) . . ?
C9 C10 C11 118.4(2) . . ?
C10 C1 H1 119.4 . . ?
C2 C1 C10 121.2(2) . . ?
C2 C1 H1 119.4 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C9 119.3(2) . . ?
C3 C4 C5 122.8(2) . . ?
C9 C4 C5 117.9(2) . . ?
C4 C9 C10 119.3(2) . . ?
C4 C9 C8 120.31(19) . . ?
C8 C9 C10 120.4(2) . . ?
C9 C8 C13 119.29(19) . . ?
C9 C8 C7 120.56(19) . . ?
C13 C8 C7 120.14(19) . . ?
C8 C13 C12 118.7(2) . . ?
C14 C13 C12 122.5(2) . . ?
C14 C13 C8 118.8(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.7(2) . . ?
C16 C15 H15 119.2 . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.3(2) . . ?
C6 C5 H5 118.9 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.7(2) . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 117.26(19) . . ?
C16 C7 C8 118.91(19) . . ?
C16 C7 C6 123.78(19) . . ?
C15 C16 C7 119.3(2) . . ?
C15 C16 C17 117.85(19) . . ?
C7 C16 C17 122.8(2) . . ?
N1 C17 C16 115.1(2) . . ?
N1 C17 C18 122.1(2) . . ?
C18 C17 C16 122.7(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.8 . . ?
C18 C19 C20 118.4(2) . . ?
C20 C19 H19 120.8 . . ?
C19 C20 C22 120.4(3) . . ?
C21 C20 C19 118.2(2) . . ?
C21 C20 C22 121.4(3) . . ?
N1 C21 C20 124.2(2) . . ?
N1 C21 H21 117.9 . . ?
C20 C21 H21 117.9 . . ?
F1 C22 F3 104.8(3) . . ?
F1 C22 C20 112.8(3) . . ?
F2 C22 F1 107.0(3) . . ?
F2 C22 F3 103.9(3) . . ?
F2 C22 C20 114.2(3) . . ?
F3 C22 C20 113.3(3) . . ?
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 1.310(4) . ?
F2 C22 1.278(4) . ?
F3 C22 1.318(4) . ?
N1 C17 1.343(3) . ?
N1 C21 1.339(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.339(3) . ?
C12 C13 1.436(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.435(3) . ?
C10 C1 1.393(3) . ?
C10 C9 1.427(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.381(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(3) . ?
C4 C9 1.418(3) . ?
C4 C5 1.433(3) . ?
C9 C8 1.422(3) . ?
C8 C13 1.424(3) . ?
C8 C7 1.427(3) . ?
C13 C14 1.386(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.392(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.339(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.446(3) . ?
C7 C16 1.412(3) . ?
C16 C17 1.496(3) . ?
C17 C18 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.374(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(4) . ?
C20 C21 1.374(4) . ?
C20 C22 1.482(4) . ?
C21 H21 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
N1 C17 C18 C19 2.1(4) . . . . ?
C12 C11 C10 C1 -179.4(2) . . . . ?
C12 C11 C10 C9 0.0(3) . . . . ?
C12 C13 C14 C15 176.2(2) . . . . ?
C11 C12 C13 C8 -0.7(3) . . . . ?
C11 C12 C13 C14 179.6(2) . . . . ?
C11 C10 C1 C2 179.6(2) . . . . ?
C11 C10 C9 C4 -179.73(19) . . . . ?
C11 C10 C9 C8 0.8(3) . . . . ?
C10 C1 C2 C3 -0.2(4) . . . . ?
C10 C9 C8 C13 -1.5(3) . . . . ?
C10 C9 C8 C7 177.92(19) . . . . ?
C1 C10 C9 C4 -0.4(3) . . . . ?
C1 C10 C9 C8 -179.8(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C9 -0.4(4) . . . . ?
C2 C3 C4 C5 178.1(2) . . . . ?
C3 C4 C9 C10 0.5(3) . . . . ?
C3 C4 C9 C8 179.9(2) . . . . ?
C3 C4 C5 C6 -177.8(2) . . . . ?
C4 C9 C8 C13 179.03(19) . . . . ?
C4 C9 C8 C7 -1.5(3) . . . . ?
C4 C5 C6 C7 -2.7(4) . . . . ?
C9 C10 C1 C2 0.2(4) . . . . ?
C9 C4 C5 C6 0.7(3) . . . . ?
C9 C8 C13 C12 1.4(3) . . . . ?
C9 C8 C13 C14 -178.85(19) . . . . ?
C9 C8 C7 C6 -0.3(3) . . . . ?
C9 C8 C7 C16 -177.93(19) . . . . ?
C8 C13 C14 C15 -3.5(3) . . . . ?
C8 C7 C16 C15 -2.9(3) . . . . ?
C8 C7 C16 C17 174.77(19) . . . . ?
C13 C12 C11 C10 0.0(4) . . . . ?
C13 C8 C7 C6 179.13(18) . . . . ?
C13 C8 C7 C16 1.5(3) . . . . ?
C13 C14 C15 C16 2.1(4) . . . . ?
C14 C15 C16 C7 1.2(3) . . . . ?
C14 C15 C16 C17 -176.6(2) . . . . ?
C15 C16 C17 N1 50.5(3) . . . . ?
C15 C16 C17 C18 -128.5(3) . . . . ?
C5 C4 C9 C10 -178.10(19) . . . . ?
C5 C4 C9 C8 1.4(3) . . . . ?
C5 C6 C7 C8 2.4(3) . . . . ?
C5 C6 C7 C16 179.9(2) . . . . ?
C6 C7 C16 C15 179.6(2) . . . . ?
C6 C7 C16 C17 -2.7(3) . . . . ?
C7 C8 C13 C12 -177.99(19) . . . . ?
C7 C8 C13 C14 1.7(3) . . . . ?
C7 C16 C17 N1 -127.3(2) . . . . ?
C7 C16 C17 C18 53.8(3) . . . . ?
C16 C17 C18 C19 -179.0(2) . . . . ?
C17 N1 C21 C20 -0.6(4) . . . . ?
C17 C18 C19 C20 -1.0(4) . . . . ?
C18 C19 C20 C21 -0.8(4) . . . . ?
C18 C19 C20 C22 -180.0(3) . . . . ?
C19 C20 C21 N1 1.7(4) . . . . ?
C19 C20 C22 F1 -43.4(4) . . . . ?
C19 C20 C22 F2 79.0(4) . . . . ?
C19 C20 C22 F3 -162.3(3) . . . . ?
C21 N1 C17 C16 179.8(2) . . . . ?
C21 N1 C17 C18 -1.3(4) . . . . ?
C21 C20 C22 F1 137.4(3) . . . . ?
C21 C20 C22 F2 -100.2(4) . . . . ?
C21 C20 C22 F3 18.5(4) . . . . ?
C22 C20 C21 N1 -179.2(3) . . . . ?
