#------------------------------------------------------------------------------
#$Date: 2022-03-05 00:20:47 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273399 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/12/7061242.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_7061242
loop_
_publ_author_name
'Yamada, Shigeyuki'
'Sato, Masaya'
'Uto, Eiji'
'Kataoka, Mitsuki'
'Morita, Masato'
'Konno, Tsutomu'
_publ_section_title
;
 Fluorinated tolane-based fluorophores bearing a branched flexible unit
 with aggregation-induced emission enhancement characteristics
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3392
_journal_page_last               3400
_journal_paper_doi               10.1039/D1NJ05822C
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C17 H11 F5 O2'
_chemical_formula_sum            'C17 H11 F5 O2'
_chemical_formula_weight         342.26
_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             2020-12-01
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-10-29 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.474(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9965(3)
_cell_length_b                   7.9831(3)
_cell_length_c                   21.5960(9)
_cell_measurement_reflns_used    7136
_cell_measurement_temperature    299
_cell_measurement_theta_max      27.1040
_cell_measurement_theta_min      2.6960
_cell_volume                     1546.30(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_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      299
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     47.00  74.00   0.25    1.21    --  -11.80  66.00  -2.00  108
  2  ω    -43.00 -18.00   0.25    1.21    --  -11.80  66.00  -2.00  100
  3  ω      9.00  35.00   0.25    1.21    --    5.00  57.00 -90.00  104
  4  ω     16.00  42.00   0.25    1.21    --    5.00  76.00-150.00  104
  5  ω      7.00  32.00   0.25    1.21    --    5.00  66.00  -2.00  100
  6  ω    -46.00  36.00   0.25    1.21    --  -11.80  57.00  60.00  328
  7  ω     21.00  71.00   0.25    1.21    --  -11.80  57.00-150.00  200
  8  ω     52.00  77.00   0.25    1.21    --  -11.80  57.00  60.00  100
  9  ω    -47.00  69.00   0.25    1.21    --  -11.80  57.00 -60.00  464
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0698509000
_diffrn_orient_matrix_UB_12      0.0227693000
_diffrn_orient_matrix_UB_13      0.0106364000
_diffrn_orient_matrix_UB_21      -0.0353113000
_diffrn_orient_matrix_UB_22      -0.0635895000
_diffrn_orient_matrix_UB_23      -0.0187739000
_diffrn_orient_matrix_UB_31      0.0113851000
_diffrn_orient_matrix_UB_32      -0.0576207000
_diffrn_orient_matrix_UB_33      0.0249234000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16469
_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         27.480
_diffrn_reflns_theta_min         2.271
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.937
_exptl_crystal_size_mid          0.674
_exptl_crystal_size_min          0.259
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0510
_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)+(0.0790P)²+0.1650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1624
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2396
_reflns_number_total             3541
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj05822c2.cif
_cod_data_source_block           tol-5f-nb
_cod_depositor_comments
'Adding full bibliography for 7061242--7061245.cif.'
_cod_database_code               7061242
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C17H11F5O2
_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.
;
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00L(H00B,H00C), C00N(H00D,H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00F(H00F), C00I(H00I)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.326
_oxdiff_exptl_absorpt_empirical_full_min 0.404
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
O001 O 0.27878(13) 0.44720(15) 0.23476(5) 0.0725(3) Uani 1 1 d . . . . .
F002 F 0.93545(15) 0.60293(16) 0.55051(6) 0.0984(4) Uani 1 1 d . . . . .
F003 F 1.08240(13) 0.56068(18) 0.66169(6) 0.1037(4) Uani 1 1 d . . . . .
F004 F 1.01361(15) 0.30285(18) 0.73520(5) 0.1086(5) Uani 1 1 d . . . . .
F005 F 0.64991(17) 0.12431(18) 0.58435(7) 0.1155(5) Uani 1 1 d . . . . .
F006 F 0.7951(2) 0.08625(18) 0.69614(7) 0.1303(6) Uani 1 1 d . . . . .
C007 C 0.37187(17) 0.4446(2) 0.28737(7) 0.0601(4) Uani 1 1 d . . . . .
O2 O 0.2044(3) 0.3957(2) 0.10513(7) 0.1257(7) Uani 1 1 d . . . . .
C009 C 0.34202(17) 0.3216(2) 0.33015(7) 0.0622(4) Uani 1 1 d . . . . .
H009 H 0.2633 0.2476 0.3215 0.075 Uiso 1 1 calc R . . . .
C00A C 0.42789(18) 0.3091(2) 0.38500(8) 0.0668(4) Uani 1 1 d . . . . .
H00A H 0.4066 0.2266 0.4134 0.080 Uiso 1 1 calc R . . . .
C00B C 0.78943(18) 0.3631(2) 0.56300(8) 0.0674(4) Uani 1 1 d . . . . .
C00C C 0.54637(18) 0.4176(2) 0.39898(8) 0.0669(4) Uani 1 1 d . . . . .
C00D C 0.90160(19) 0.4712(2) 0.58490(8) 0.0681(4) Uani 1 1 d . . . . .
C00E C 0.97716(18) 0.4512(2) 0.64178(9) 0.0723(5) Uani 1 1 d . . . . .
C00F C 0.48970(19) 0.5532(2) 0.30058(9) 0.0716(4) Uani 1 1 d . . . . .
H00F H 0.5109 0.6355 0.2721 0.086 Uiso 1 1 calc R . . . .
C00G C 0.9426(2) 0.3219(2) 0.67929(8) 0.0760(5) Uani 1 1 d . . . . .
C00H C 0.6358(2) 0.4026(2) 0.45668(8) 0.0744(5) Uani 1 1 d . . . . .
C00I C 0.57550(19) 0.5396(2) 0.35589(9) 0.0740(5) Uani 1 1 d . . . . .
H00I H 0.6544 0.6134 0.3645 0.089 Uiso 1 1 calc R . . . .
C00J C 0.7081(2) 0.3854(2) 0.50456(8) 0.0758(5) Uani 1 1 d . . . . .
C00K C 0.7581(2) 0.2331(2) 0.60216(9) 0.0778(5) Uani 1 1 d . . . . .
C00L C 0.3063(2) 0.5675(2) 0.18808(9) 0.0789(5) Uani 1 1 d . . . . .
H00B H 0.4045 0.5500 0.1736 0.095 Uiso 1 1 calc R . . . .
H00C H 0.3024 0.6799 0.2050 0.095 Uiso 1 1 calc R . . . .
C00M C 0.8325(2) 0.2127(2) 0.65939(9) 0.0840(5) Uani 1 1 d . . . . .
C00N C 0.1907(3) 0.5472(2) 0.13600(9) 0.0858(6) Uani 1 1 d . . . . .
H00D H 0.0929 0.5532 0.1519 0.103 Uiso 1 1 calc R . . . .
H00E H 0.1985 0.6386 0.1068 0.103 Uiso 1 1 calc R . . . .
C10 C 0.2086(7) 0.3932(4) 0.04747(14) 0.192(2) Uani 1 1 d . . . . .
H10A H 0.1181 0.4400 0.0283 0.289 Uiso 1 1 calc GR . . . .
H10B H 0.2189 0.2796 0.0338 0.289 Uiso 1 1 calc GR . . . .
H10C H 0.2921 0.4579 0.0360 0.289 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'
O O 0.0106 0.0060 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -8 20 0.3220
-2 -7 25 0.2922
-12 1 13 0.1481
-4 8 -20 0.3365
12 -2 -11 0.2013
0 -7 23 0.3066
-12 -1 9 0.0982
-3 7 -21 0.3561
3 7 -24 0.3678
12 1 -9 0.1602
-12 -2 5 0.1691
-12 -3 6 0.1623
12 -1 6 0.2858
-10 -7 -3 0.3062
9 1 19 0.3509
6 9 -10 0.3596
6 2 26 0.3498
3 11 -7 0.3775
6 -8 -17 0.2618
-6 5 25 0.2990
10 -3 -19 0.1980
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
C007 O001 C00L 118.12(13) . . ?
O001 C007 C009 115.41(13) . . ?
O001 C007 C00F 125.15(15) . . ?
C00F C007 C009 119.44(15) . . ?
C10 O2 C00N 120.2(2) . . ?
C007 C009 H009 119.9 . . ?
C00A C009 C007 120.20(15) . . ?
C00A C009 H009 119.9 . . ?
C009 C00A H00A 119.5 . . ?
C009 C00A C00C 121.02(16) . . ?
C00C C00A H00A 119.5 . . ?
C00D C00B C00J 122.50(18) . . ?
C00K C00B C00D 115.95(15) . . ?
C00K C00B C00J 121.54(17) . . ?
C00A C00C C00H 120.38(17) . . ?
C00I C00C C00A 118.33(16) . . ?
C00I C00C C00H 121.29(16) . . ?
F002 C00D C00B 119.53(15) . . ?
F002 C00D C00E 118.21(16) . . ?
C00E C00D C00B 122.23(17) . . ?
F003 C00E C00D 120.24(18) . . ?
F003 C00E C00G 119.56(17) . . ?
C00G C00E C00D 120.17(17) . . ?
C007 C00F H00F 120.0 . . ?
C00I C00F C007 119.93(17) . . ?
C00I C00F H00F 120.0 . . ?
F004 C00G C00E 120.72(18) . . ?
F004 C00G C00M 119.90(19) . . ?
C00E C00G C00M 119.37(17) . . ?
C00J C00H C00C 178.0(2) . . ?
C00C C00I H00I 119.5 . . ?
C00F C00I C00C 121.09(16) . . ?
C00F C00I H00I 119.5 . . ?
C00H C00J C00B 177.7(2) . . ?
F005 C00K C00B 119.34(17) . . ?
F005 C00K C00M 118.41(19) . . ?
C00M C00K C00B 122.24(18) . . ?
O001 C00L H00B 110.1 . . ?
O001 C00L H00C 110.1 . . ?
O001 C00L C00N 108.19(15) . . ?
H00B C00L H00C 108.4 . . ?
C00N C00L H00B 110.1 . . ?
C00N C00L H00C 110.1 . . ?
F006 C00M C00G 120.23(18) . . ?
F006 C00M C00K 119.7(2) . . ?
C00G C00M C00K 120.04(19) . . ?
O2 C00N C00L 112.08(18) . . ?
O2 C00N H00D 109.2 . . ?
O2 C00N H00E 109.2 . . ?
C00L C00N H00D 109.2 . . ?
C00L C00N H00E 109.2 . . ?
H00D C00N H00E 107.9 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
O001 C007 1.3581(19) . ?
O001 C00L 1.428(2) . ?
F002 C00D 1.336(2) . ?
F003 C00E 1.335(2) . ?
F004 C00G 1.330(2) . ?
F005 C00K 1.338(2) . ?
F006 C00M 1.343(2) . ?
C007 C009 1.388(2) . ?
C007 C00F 1.382(2) . ?
O2 C00N 1.391(2) . ?
O2 C10 1.249(3) . ?
C009 H009 0.9300 . ?
C009 C00A 1.366(2) . ?
C00A H00A 0.9300 . ?
C00A C00C 1.388(2) . ?
C00B C00D 1.383(2) . ?
C00B C00J 1.420(2) . ?
C00B C00K 1.381(3) . ?
C00C C00H 1.435(2) . ?
C00C C00I 1.386(3) . ?
C00D C00E 1.366(2) . ?
C00E C00G 1.362(3) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.375(3) . ?
C00G C00M 1.364(3) . ?
C00H C00J 1.186(2) . ?
C00I H00I 0.9300 . ?
C00K C00M 1.368(3) . ?
C00L H00B 0.9700 . ?
C00L H00C 0.9700 . ?
C00L C00N 1.480(3) . ?
C00N H00D 0.9700 . ?
C00N H00E 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.8062 -7.5730 19.8106 -0.2276 -0.0248 0.9734
-2.0984 -6.5238 24.6067 0.2598 0.0270 0.9653
-11.8079 1.1116 12.8676 0.9870 0.1047 0.1222
-3.9001 7.5752 -19.6861 0.2355 0.0256 -0.9715
11.9562 -1.6306 -11.3521 -0.9930 -0.1054 -0.0529
-0.3961 -7.2273 23.3206 0.1112 0.0357 0.9932
-12.3435 -0.6551 9.0512 0.9436 0.3076 0.1228
-3.1899 7.2417 -21.3455 0.1607 0.0529 -0.9856
2.5465 6.9336 -23.5941 -0.2710 -0.0879 -0.9586
12.3446 0.6520 -9.0419 -0.9436 -0.3076 -0.1224
-11.9999 -2.0000 5.0006 0.8459 0.4570 0.1033
-11.9999 -3.0000 6.0006 0.8337 0.5018 0.1858
11.9999 -1.0000 5.9995 -0.7972 -0.4728 0.3438
-9.9999 -7.0000 -2.9997 0.5072 0.8546 0.2147
9.0000 1.0000 18.9999 -0.4038 -0.7381 0.5184
5.9999 9.0000 -10.0002 -0.3205 -0.5964 -0.6995
6.0000 2.0000 26.0002 -0.0970 -0.8272 0.6011
2.9999 11.0000 -7.0000 -0.0335 -0.6740 -0.7741
6.0000 -8.0000 -17.0008 -0.7821 0.6160 0.1056
-5.9999 5.0000 25.0008 0.7989 -0.5754 0.2667
9.9999 -3.0000 -19.0009 -0.9689 0.1944 -0.1869
