#------------------------------------------------------------------------------
#$Date: 2021-07-06 04:26:30 +0300 (Tue, 06 Jul 2021) $
#$Revision: 267261 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/39/1563948.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_1563948
loop_
_publ_author_name
'Xiong, Zuping'
'Zhang, Xiaoxiao'
'Liu, Longxiang'
'Zhu, Qiaozhi'
'Wang, Zhenni'
'Feng, Hui'
'Qian, Zhaosheng'
_publ_section_title
;
 Achieving Highly Efficient Aggregation-Induced Emission, Reversible and
 Irreversible Photochromism by Heavy Halogen-Regulated Photophysics and
 D-A Molecular Pattern-Controlled Photochemistry of Through-Space
 Conjugated Lumingens
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02168K
_journal_year                    2021
_chemical_formula_moiety         'C21 H14 F N'
_chemical_formula_sum            'C21 H14 F N'
_chemical_formula_weight         299.33
_chemical_name_common            TPAN-F
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-01-06 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                106.884(5)
_cell_angle_beta                 104.687(5)
_cell_angle_gamma                91.445(5)
_cell_formula_units_Z            2
_cell_length_a                   8.4617(8)
_cell_length_b                   9.9195(9)
_cell_length_c                   10.0112(10)
_cell_measurement_reflns_used    1659
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.19
_cell_measurement_theta_min      2.50
_cell_volume                     773.36(13)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.1119
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16287
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_min         2.158
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0706 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.9081.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1154
_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)+(0.0445P)²+0.1358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1276
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1873
_reflns_number_total             3176
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc02168k2.cif
_cod_data_source_block           mo_0610_1_0m
_cod_database_code               1563948
_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   0.992
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
F001 F 0.78301(17) 0.80296(14) 0.16399(15) 0.0373(4) Uani 1 1 d . . . . .
N002 N 0.0955(3) 0.3756(2) 0.1373(2) 0.0356(5) Uani 1 1 d . . . . .
C003 C 0.4667(3) 0.2500(2) 0.2688(2) 0.0235(5) Uani 1 1 d . . . . .
C004 C 0.4093(3) 0.3586(2) 0.2203(2) 0.0245(5) Uani 1 1 d . . . . .
C005 C 0.3582(3) 0.1213(2) 0.2492(3) 0.0248(5) Uani 1 1 d . . . . .
C006 C 0.6928(3) 0.6949(2) 0.1792(2) 0.0274(6) Uani 1 1 d . . . . .
C007 C 0.2335(3) 0.3629(2) 0.1717(3) 0.0272(6) Uani 1 1 d . . . . .
C008 C 0.6428(3) 0.2516(2) 0.3426(2) 0.0240(5) Uani 1 1 d . . . . .
C009 C 0.6521(3) 0.4534(2) 0.1622(2) 0.0267(6) Uani 1 1 d . . . . .
H009 H 0.685175 0.360528 0.139878 0.032 Uiso 1 1 calc R . . . .
C00A C 0.5534(3) 0.7244(2) 0.2232(2) 0.0281(6) Uani 1 1 d . . . . .
H00A H 0.520256 0.817318 0.242853 0.034 Uiso 1 1 calc R . . . .
C00B C 0.5110(3) 0.4775(2) 0.2092(2) 0.0236(5) Uani 1 1 d . . . . .
C00C C 0.4624(3) 0.6144(2) 0.2380(2) 0.0268(6) Uani 1 1 d . . . . .
H00C H 0.365185 0.632169 0.268248 0.032 Uiso 1 1 calc R . . . .
C00D C 0.3577(3) 0.0720(3) 0.3663(3) 0.0294(6) Uani 1 1 d . . . . .
H00D H 0.423781 0.123524 0.460630 0.035 Uiso 1 1 calc R . . . .
C00E C 0.7276(3) 0.1364(2) 0.2938(3) 0.0296(6) Uani 1 1 d . . . . .
H00E H 0.670759 0.056373 0.215723 0.035 Uiso 1 1 calc R . . . .
C00F C 0.7452(3) 0.5620(2) 0.1473(3) 0.0275(6) Uani 1 1 d . . . . .
H00F H 0.842059 0.545441 0.116184 0.033 Uiso 1 1 calc R . . . .
C00G C 0.7279(3) 0.3659(2) 0.4610(3) 0.0283(6) Uani 1 1 d . . . . .
H00G H 0.672303 0.444976 0.496134 0.034 Uiso 1 1 calc R . . . .
C00H C 0.2614(3) 0.0429(2) 0.1118(3) 0.0309(6) Uani 1 1 d . . . . .
H00H H 0.259337 0.075313 0.030976 0.037 Uiso 1 1 calc R . . . .
C00I C 0.8927(3) 0.3649(3) 0.5276(3) 0.0327(6) Uani 1 1 d . . . . .
H00I H 0.948597 0.441839 0.609696 0.039 Uiso 1 1 calc R . . . .
C00J C 0.2622(3) -0.0507(3) 0.3466(3) 0.0343(6) Uani 1 1 d . . . . .
H00J H 0.260888 -0.081824 0.427581 0.041 Uiso 1 1 calc R . . . .
C00K C 0.1680(3) -0.0822(3) 0.0920(3) 0.0364(7) Uani 1 1 d . . . . .
H00K H 0.103965 -0.135745 -0.002398 0.044 Uiso 1 1 calc R . . . .
C00L C 0.1681(3) -0.1287(3) 0.2093(3) 0.0364(7) Uani 1 1 d . . . . .
H00L H 0.103919 -0.213931 0.195820 0.044 Uiso 1 1 calc R . . . .
C00M C 0.8928(3) 0.1375(3) 0.3577(3) 0.0356(6) Uani 1 1 d . . . . .
H00M H 0.949669 0.059822 0.321461 0.043 Uiso 1 1 calc R . . . .
C00N C 0.9759(3) 0.2518(3) 0.4746(3) 0.0364(6) Uani 1 1 d . . . . .
H00N H 1.089652 0.252529 0.518352 0.044 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'
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
C004 C003 C005 122.3(2) . . ?
C004 C003 C008 121.7(2) . . ?
C008 C003 C005 115.93(19) . . ?
C003 C004 C007 119.2(2) . . ?
C003 C004 C00B 126.1(2) . . ?
C007 C004 C00B 114.6(2) . . ?
C00D C005 C003 120.9(2) . . ?
C00H C005 C003 120.6(2) . . ?
C00H C005 C00D 118.5(2) . . ?
F001 C006 C00A 118.2(2) . . ?
F001 C006 C00F 118.3(2) . . ?
C00A C006 C00F 123.5(2) . . ?
N002 C007 C004 175.6(2) . . ?
C00E C008 C003 119.8(2) . . ?
C00E C008 C00G 118.4(2) . . ?
C00G C008 C003 121.8(2) . . ?
C00F C009 C00B 121.3(2) . . ?
C006 C00A C00C 117.8(2) . . ?
C009 C00B C004 120.6(2) . . ?
C009 C00B C00C 118.3(2) . . ?
C00C C00B C004 120.9(2) . . ?
C00A C00C C00B 121.2(2) . . ?
C00J C00D C005 120.7(2) . . ?
C00M C00E C008 120.8(2) . . ?
C006 C00F C009 117.7(2) . . ?
C00I C00G C008 120.6(2) . . ?
C00K C00H C005 120.6(2) . . ?
C00N C00I C00G 120.1(2) . . ?
C00D C00J C00L 120.3(2) . . ?
C00L C00K C00H 120.0(2) . . ?
C00K C00L C00J 119.8(2) . . ?
C00E C00M C00N 120.2(2) . . ?
C00I C00N C00M 119.9(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
F001 C006 1.366(3) . ?
N002 C007 1.152(3) . ?
C003 C004 1.358(3) . ?
C003 C005 1.488(3) . ?
C003 C008 1.483(3) . ?
C004 C007 1.449(3) . ?
C004 C00B 1.489(3) . ?
C005 C00D 1.396(3) . ?
C005 C00H 1.394(3) . ?
C006 C00A 1.370(3) . ?
C006 C00F 1.376(3) . ?
C008 C00E 1.397(3) . ?
C008 C00G 1.398(3) . ?
C009 C00B 1.393(3) . ?
C009 C00F 1.383(3) . ?
C00A C00C 1.384(3) . ?
C00B C00C 1.398(3) . ?
C00D C00J 1.380(3) . ?
C00E C00M 1.380(3) . ?
C00G C00I 1.386(3) . ?
C00H C00K 1.390(3) . ?
C00I C00N 1.385(4) . ?
C00J C00L 1.385(4) . ?
C00K C00L 1.380(4) . ?
C00M C00N 1.386(3) . ?
