#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:05:33 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257738 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/94/7059495.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_7059495
loop_
_publ_author_name
'Morita, Masato'
'Yamada, Shigeyuki'
'Konno, Tsutomu'
_publ_section_title
;
 Fluorine-induced emission enhancement of tolanes via formation of tight
 molecular aggregates
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6704
_journal_page_last               6708
_journal_paper_doi               10.1039/D0NJ01268H
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C16 H10 F4 O2'
_chemical_formula_sum            'C16 H10 F4 O2'
_chemical_formula_weight         310.24
_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             2019-09-27
_audit_creation_method
;
Olex2 1.3
(compiled Sep 10 2019 10:52:38 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2020-02-05 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                100.778(5)
_cell_angle_beta                 96.710(4)
_cell_angle_gamma                113.627(5)
_cell_formula_units_Z            2
_cell_length_a                   7.3516(4)
_cell_length_b                   8.5060(5)
_cell_length_c                   12.5385(7)
_cell_measurement_reflns_used    3930
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.6390
_cell_measurement_theta_min      2.6660
_cell_volume                     689.46(8)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  22.00   0.25    1.35    --    5.00  76.00 150.00  104
  2  ω     27.00  53.00   0.25    1.35    --    5.00  76.00 150.00  104
  3  ω     40.00  77.00   0.25    1.35    --  -11.60  57.00  30.00  148
  4  ω    -51.00  -9.00   0.25    1.35    --  -11.60  76.00 120.00  168
  5  ω    -33.00  -6.00   0.25    1.35    --  -11.60  57.00 -30.00  108
  6  ω      1.00  70.00   0.25    1.35    --  -11.60  57.00 -30.00  276
  7  ω    -53.00  28.00   0.25    1.35    --  -11.60  76.00-120.00  324
  8  ω    -47.00  15.00   0.25    1.35    --  -11.60  57.00  30.00  248
  9  ω    -66.00  76.00   0.25    1.35    --  -11.60  19.00 150.00  568
;
_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      0.1016826000
_diffrn_orient_matrix_UB_12      0.0357441000
_diffrn_orient_matrix_UB_13      0.0301758000
_diffrn_orient_matrix_UB_21      0.0333447000
_diffrn_orient_matrix_UB_22      -0.0105833000
_diffrn_orient_matrix_UB_23      -0.0505825000
_diffrn_orient_matrix_UB_31      0.0128994000
_diffrn_orient_matrix_UB_32      0.0864889000
_diffrn_orient_matrix_UB_33      -0.0021674000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9710
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.705
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83125
_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    1.494
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.207
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0434
_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)+(0.0703P)²+0.0451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1455
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1980
_reflns_number_total             3147
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj01268h2.cif
_cod_data_source_block           c1_4f_c1
_cod_depositor_comments
;Adding full bibliography for 7059490--7059495.cif.

 Adding full bibliography for 7059490--7059495.cif.
;
_cod_original_cell_volume        689.46(7)
_cod_database_code               7059495
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H10F4O2
_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 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00G(H00G), C00I(H00I), C00J(H00J)
2.b Idealised Me refined as rotating group:
 C00L(H00A,H00B,H00C), C00M(H00E,H00F,H00H)
;
_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 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.773
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 0.58720(16) 0.82813(13) 0.44327(8) 0.0867(4) Uani 1 1 d . . . . .
F002 F 0.78065(16) 1.17340(13) 0.46791(8) 0.0865(3) Uani 1 1 d . . . . .
F3 F 0.24794(16) 0.75560(14) 0.08341(9) 0.0890(4) Uani 1 1 d . . . . .
F4 F 0.44036(19) 1.10478(14) 0.10723(9) 0.0923(4) Uani 1 1 d . . . . .
O005 O -0.1496(2) -0.28552(14) 0.21546(11) 0.0857(4) Uani 1 1 d . . . . .
O006 O 0.7017(2) 1.32467(15) 0.29148(12) 0.0937(4) Uani 1 1 d . . . . .
C007 C 0.1147(2) 0.25346(19) 0.23729(13) 0.0608(4) Uani 1 1 d . . . . .
C008 C 0.5449(2) 0.8946(2) 0.35960(13) 0.0633(4) Uani 1 1 d . . . . .
C009 C -0.0700(2) -0.10984(19) 0.21692(14) 0.0621(4) Uani 1 1 d . . . . .
C00A C 0.4062(2) 0.78014(19) 0.26401(13) 0.0610(4) Uani 1 1 d . . . . .
C00B C 0.6448(2) 1.0741(2) 0.37228(13) 0.0644(4) Uani 1 1 d . . . . .
C00C C 0.4756(2) 1.0373(2) 0.19175(14) 0.0644(4) Uani 1 1 d . . . . .
C00D C 0.1500(2) 0.1845(2) 0.32559(14) 0.0648(4) Uani 1 1 d . . . . .
H00D H 0.236512 0.260765 0.392173 0.078 Uiso 1 1 calc R U . . .
C00E C 0.6101(2) 1.15107(19) 0.28905(14) 0.0639(4) Uani 1 1 d . . . . .
C00F C 0.3772(2) 0.8583(2) 0.17958(13) 0.0646(4) Uani 1 1 d . . . . .
C00G C 0.0589(2) 0.0053(2) 0.31550(14) 0.0662(4) Uani 1 1 d . . . . .
H00G H 0.083698 -0.039121 0.375164 0.079 Uiso 1 1 calc R U . . .
C00H C 0.3011(2) 0.5945(2) 0.25335(14) 0.0667(4) Uani 1 1 d . . . . .
C00I C -0.0181(2) 0.1369(2) 0.13998(13) 0.0673(4) Uani 1 1 d . . . . .
H00I H -0.045738 0.181007 0.080678 0.081 Uiso 1 1 calc R U . . .
C00J C -0.1100(2) -0.0437(2) 0.12960(13) 0.0664(4) Uani 1 1 d . . . . .
H00J H -0.198656 -0.120431 0.063710 0.080 Uiso 1 1 calc R U . . .
C00K C 0.2153(2) 0.4400(2) 0.24631(14) 0.0678(4) Uani 1 1 d . . . . .
C00L C -0.2705(4) -0.4111(2) 0.11416(18) 0.1015(7) Uani 1 1 d . . . . .
H00A H -0.191742 -0.399062 0.057755 0.152 Uiso 1 1 calc R U . . .
H00B H -0.386683 -0.390410 0.091824 0.152 Uiso 1 1 calc R U . . .
H00C H -0.315032 -0.528866 0.124360 0.152 Uiso 1 1 calc R U . . .
C00M C 0.7461(4) 1.4561(2) 0.38762(19) 0.1116(8) Uani 1 1 d . . . . .
H00E H 0.737178 1.557302 0.368522 0.167 Uiso 1 1 calc R U . . .
H00F H 0.881184 1.490242 0.427815 0.167 Uiso 1 1 calc R U . . .
H00H H 0.650687 1.411735 0.433112 0.167 Uiso 1 1 calc R U . . .
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
1 10 -8 0.1192
5 6 -11 0.1319
9 -1 -11 0.1380
8 -11 -3 0.1062
-8 -1 12 0.1174
-3 10 6 0.1697
-2 8 -15 0.1018
0 2 -17 0.0856
2 -10 -7 0.1003
3 -12 7 0.1097
1 -4 17 0.1134
0 10 2 0.1423
6 -6 13 0.1201
-6 1 -12 0.1367
-2 -5 -10 0.1154
-4 2 -15 0.1201
4 -1 14 0.1144
10 -6 1 0.1477
10 0 -2 0.1660
10 -2 -1 0.1590
3 8 -13 0.1156
2 6 -16 0.1074
-4 12 -6 0.1676
6 -3 13 0.1168
3 6 7 0.1465
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
C009 O005 C00L 118.03(14) . . ?
C00E O006 C00M 121.54(15) . . ?
C00D C007 C00K 120.81(15) . . ?
C00I C007 C00D 118.33(14) . . ?
C00I C007 C00K 120.85(14) . . ?
F001 C008 C00A 119.06(14) . . ?
F001 C008 C00B 118.23(14) . . ?
C00B C008 C00A 122.70(15) . . ?
O005 C009 C00G 115.35(15) . . ?
O005 C009 C00J 124.86(15) . . ?
C00J C009 C00G 119.79(15) . . ?
C008 C00A C00F 115.55(14) . . ?
C008 C00A C00H 121.82(14) . . ?
C00F C00A C00H 122.63(15) . . ?
F002 C00B C008 117.95(15) . . ?
F002 C00B C00E 120.80(14) . . ?
C008 C00B C00E 121.24(15) . . ?
F4 C00C C00E 118.99(14) . . ?
F4 C00C C00F 119.23(15) . . ?
C00F C00C C00E 121.77(15) . . ?
C007 C00D H00D 119.6 . . ?
C00G C00D C007 120.70(15) . . ?
C00G C00D H00D 119.6 . . ?
O006 C00E C00B 126.39(16) . . ?
O006 C00E C00C 116.93(15) . . ?
C00B C00E C00C 116.60(14) . . ?
F3 C00F C00A 119.14(14) . . ?
F3 C00F C00C 118.78(15) . . ?
C00C C00F C00A 122.08(15) . . ?
C009 C00G H00G 119.9 . . ?
C00D C00G C009 120.29(16) . . ?
C00D C00G H00G 119.9 . . ?
C00K C00H C00A 178.8(2) . . ?
C007 C00I H00I 119.5 . . ?
C00J C00I C007 121.04(15) . . ?
C00J C00I H00I 119.5 . . ?
C009 C00J C00I 119.82(15) . . ?
C009 C00J H00J 120.1 . . ?
C00I C00J H00J 120.1 . . ?
C00H C00K C007 179.08(18) . . ?
O005 C00L H00A 109.5 . . ?
O005 C00L H00B 109.5 . . ?
O005 C00L H00C 109.5 . . ?
H00A C00L H00B 109.5 . . ?
H00A C00L H00C 109.5 . . ?
H00B C00L H00C 109.5 . . ?
O006 C00M H00E 109.5 . . ?
O006 C00M H00F 109.5 . . ?
O006 C00M H00H 109.5 . . ?
H00E C00M H00F 109.5 . . ?
H00E C00M H00H 109.5 . . ?
H00F C00M H00H 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
F001 C008 1.3431(18) . ?
F002 C00B 1.3469(18) . ?
F3 C00F 1.3390(18) . ?
F4 C00C 1.3425(18) . ?
O005 C009 1.3646(18) . ?
O005 C00L 1.418(2) . ?
O006 C00E 1.3477(19) . ?
O006 C00M 1.386(2) . ?
C007 C00D 1.392(2) . ?
C007 C00I 1.385(2) . ?
C007 C00K 1.432(2) . ?
C008 C00A 1.381(2) . ?
C008 C00B 1.370(2) . ?
C009 C00G 1.384(2) . ?
C009 C00J 1.374(2) . ?
C00A C00F 1.390(2) . ?
C00A C00H 1.424(2) . ?
C00B C00E 1.382(2) . ?
C00C C00E 1.383(2) . ?
C00C C00F 1.367(2) . ?
C00D H00D 0.9300 . ?
C00D C00G 1.370(2) . ?
C00G H00G 0.9300 . ?
C00H C00K 1.188(2) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.381(2) . ?
C00J H00J 0.9300 . ?
C00L H00A 0.9600 . ?
C00L H00B 0.9600 . ?
C00L H00C 0.9600 . ?
C00M H00E 0.9600 . ?
C00M H00F 0.9600 . ?
C00M H00H 0.9600 . ?
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
F001 C008 C00A C00F -177.42(14) . . . . ?
F001 C008 C00A C00H 2.4(2) . . . . ?
F001 C008 C00B F002 0.4(2) . . . . ?
F001 C008 C00B C00E 179.35(14) . . . . ?
F002 C00B C00E O006 0.3(3) . . . . ?
F002 C00B C00E C00C 176.81(13) . . . . ?
F4 C00C C00E O006 -1.5(2) . . . . ?
F4 C00C C00E C00B -178.35(14) . . . . ?
F4 C00C C00F F3 -0.1(2) . . . . ?
F4 C00C C00F C00A -179.73(14) . . . . ?
O005 C009 C00G C00D 178.92(13) . . . . ?
O005 C009 C00J C00I -179.02(15) . . . . ?
C007 C00D C00G C009 0.1(3) . . . . ?
C007 C00I C00J C009 0.1(3) . . . . ?
C008 C00A C00F F3 178.71(13) . . . . ?
C008 C00A C00F C00C -1.7(2) . . . . ?
C008 C00B C00E O006 -178.69(15) . . . . ?
C008 C00B C00E C00C -2.1(2) . . . . ?
C00A C008 C00B F002 -178.49(14) . . . . ?
C00A C008 C00B C00E 0.5(3) . . . . ?
C00B C008 C00A C00F 1.4(2) . . . . ?
C00B C008 C00A C00H -178.72(15) . . . . ?
C00D C007 C00I C00J -1.4(2) . . . . ?
C00E C00C C00F F3 179.64(14) . . . . ?
C00E C00C C00F C00A 0.0(3) . . . . ?
C00F C00C C00E O006 178.78(14) . . . . ?
C00F C00C C00E C00B 1.9(2) . . . . ?
C00G C009 C00J C00I 1.3(3) . . . . ?
C00H C00A C00F F3 -1.1(2) . . . . ?
C00H C00A C00F C00C 178.47(15) . . . . ?
C00I C007 C00D C00G 1.3(2) . . . . ?
C00J C009 C00G C00D -1.4(3) . . . . ?
C00K C007 C00D C00G -177.79(14) . . . . ?
C00K C007 C00I C00J 177.72(14) . . . . ?
C00L O005 C009 C00G -175.32(16) . . . . ?
C00L O005 C009 C00J 5.0(3) . . . . ?
C00M O006 C00E C00B -38.5(3) . . . . ?
C00M O006 C00E C00C 144.97(19) . . . . ?
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
0.5083 10.4876 -8.1036 0.1820 0.3159 0.9312
4.7907 6.4987 -11.2454 0.3801 0.6598 0.6482
8.7072 -1.4468 -11.0876 0.4991 0.8665 0.0112
7.5015 -10.5005 -3.0256 0.2961 0.5143 -0.8049
-8.0830 -0.5748 11.6455 -0.4910 -0.8525 -0.1792
-2.5214 10.1267 5.7397 0.2788 -0.4816 0.8309
-1.9096 8.2545 -14.8354 -0.3468 0.5994 0.7214
-0.3198 1.8367 -17.3864 -0.4915 0.8493 0.1924
2.3868 -9.5331 -7.1781 -0.3147 0.5436 -0.7782
2.7870 -11.6099 7.3133 0.0891 -0.1541 -0.9840
0.7644 -3.6516 17.3377 0.4704 -0.8128 -0.3435
0.0010 9.9948 2.0063 0.4179 -0.2072 0.8601
6.0013 -6.0032 13.0014 0.7880 -0.3940 -0.4700
-6.0014 1.0050 -12.0038 -0.9365 0.3964 0.0355
-2.0019 -4.9935 -10.0066 -0.6840 0.4923 -0.4360
-4.0021 2.0056 -15.0045 -0.7880 0.6043 0.1544
4.0020 -1.0057 14.0047 0.7936 -0.5643 -0.0657
9.9986 -5.9986 0.9966 0.8323 0.3465 -0.3920
9.9984 0.0000 -2.0012 0.9563 0.4346 0.1333
9.9985 -1.9995 -1.0020 0.9150 0.4052 -0.0418
2.9978 8.0016 -13.0007 0.1985 0.6729 0.7589
1.9972 6.0038 -16.0030 -0.0652 0.8125 0.5797
-3.9999 11.9976 -5.9955 -0.1588 0.0429 0.9991
6.0014 -3.0045 13.0031 0.8952 -0.4258 -0.2106
3.0013 5.9943 7.0059 0.7308 -0.3177 0.5420
