#------------------------------------------------------------------------------
#$Date: 2022-09-06 12:57:15 +0300 (Tue, 06 Sep 2022) $
#$Revision: 277661 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/73/1567383.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_1567383
loop_
_publ_author_name
'Feng, Chi'
'Seki, Tomohiro'
'Sakamoto, Shunichi'
'Sasaki, Toshiyuki'
'Takamizawa, Satoshi'
'Ito, Hajime'
_publ_section_title
;
 Mechanical deformation and multiple thermal restoration of organic
 crystals: reversible multi-stage shape-changing effect with
 luminescence-color changes
;
_journal_issue                   33
_journal_name_full               'Chemical Science'
_journal_page_first              9544
_journal_page_last               9551
_journal_paper_doi               10.1039/D2SC03414J
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         '0.5(C22 H16 Au2 Br2 F8 N4)'
_chemical_formula_sum            'C11 H8 Au Br F4 N2'
_chemical_formula_weight         521.07
_chemical_name_systematic
'1-bromo-2,3,5,6-tetrafluorobenzenyl(1,3-dimethylimidazolin-2-ylidene)gold complex'
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-01 deposited with the CCDC.	2022-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9752(7)
_cell_length_b                   6.8244(4)
_cell_length_c                   15.5938(10)
_cell_measurement_reflns_used    4754
_cell_measurement_temperature    363
_cell_measurement_theta_max      25.0580
_cell_measurement_theta_min      2.5930
_cell_volume                     1380.80(14)
_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      363
_diffrn_detector                 'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  -2.00   0.50    3.27    --   -2.10   3.00   7.00   82
  2  ω     26.00  56.00   0.50    3.27    --    2.10  43.00-150.00   60
  3  ω    -85.00  33.00   0.50    3.27    --    2.10  43.00 -90.00  236
  4  ω     64.00  92.00   0.50    3.27    --    2.10  43.00 -90.00   56
  5  ω    -60.00 -35.00   0.50    3.27    --    2.10  57.00 -30.00   50
  6  ω    -78.00 -53.00   0.50    3.27    --    2.10  43.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0544975000
_diffrn_orient_matrix_UB_12      -0.0034731000
_diffrn_orient_matrix_UB_13      0.0011384000
_diffrn_orient_matrix_UB_21      -0.0042077000
_diffrn_orient_matrix_UB_22      0.0453025000
_diffrn_orient_matrix_UB_23      -0.0048322000
_diffrn_orient_matrix_UB_31      -0.0002625000
_diffrn_orient_matrix_UB_32      -0.0021331000
_diffrn_orient_matrix_UB_33      -0.1038291000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12492
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.243
_diffrn_reflns_theta_min         2.042
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    13.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19931
_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    2.507
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.710
_refine_diff_density_min         -1.490
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1812
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0387
_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)+(0.0627P)²+2.3605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1187
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1338
_reflns_number_total             1812
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc03414j6.cif
_cod_data_source_block           hyo-307-ht
_cod_depositor_comments
'Adding full bibliography for 1567382--1567387.cif.'
_cod_database_code               1567383
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H N F Au Br'
_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   0.613
_shelx_estimated_absorpt_t_min   0.121
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Rigid body (RIGU) restrains
 C00I, C9, N8, C00D, N007
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: H00A(0.5) H00B(0.5) H00C(0.5) H00D(0.5) H00E(0.5) H00F(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C9(H9)
4.b Idealised Me refined as rotating group:
 C00B(H00A,H00B,H00C), C00H(H00D,H00E,H00F)
;
_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 3.617
_oxdiff_exptl_absorpt_empirical_full_min 0.483
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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
Au01 Au 0.45122(3) 0.250000 0.47822(3) 0.0723(2) Uani 1 2 d S T P . .
Br02 Br -0.03150(14) 0.250000 0.63976(16) 0.1365(7) Uani 1 2 d S T P . .
F003 F 0.2260(6) 0.250000 0.3906(4) 0.104(2) Uani 1 2 d S T P . .
F004 F 0.0371(5) 0.250000 0.4540(7) 0.113(3) Uani 1 2 d S T P . .
F6 F 0.3635(6) 0.250000 0.6691(4) 0.114(3) Uani 1 2 d S T P . .
F5 F 0.1752(8) 0.250000 0.7327(5) 0.149(3) Uani 1 2 d S T P . .
N007 N 0.6831(8) 0.250000 0.4775(6) 0.079(2) Uani 1 2 d S TU P . .
C008 C 0.2180(9) 0.250000 0.4765(6) 0.070(2) Uani 1 2 d S T P . .
N8 N 0.6236(8) 0.250000 0.3475(7) 0.090(2) Uani 1 2 d S TU P . .
C00A C 0.1205(9) 0.250000 0.5055(8) 0.076(3) Uani 1 2 d S T P . .
C00B C 0.6855(11) 0.250000 0.5713(8) 0.095(3) Uani 1 2 d S T P . .
H00A H 0.744775 0.321512 0.590794 0.142 Uiso 0.5 1 calc GR . . A -1
H00B H 0.689240 0.117513 0.591796 0.142 Uiso 0.5 1 calc GR . . A -1
H00C H 0.624110 0.310975 0.592971 0.142 Uiso 0.5 1 calc GR . . A -1
C00C C 0.3067(8) 0.250000 0.5265(6) 0.066(2) Uani 1 2 d S T P . .
C00D C 0.5967(8) 0.250000 0.4313(7) 0.0703(19) Uani 1 2 d S TU P . .
C00E C 0.1833(12) 0.250000 0.6464(8) 0.092(3) Uani 1 2 d S T P . .
C00F C 0.1024(9) 0.250000 0.5956(9) 0.082(3) Uani 1 2 d S T P . .
C00G C 0.2859(10) 0.250000 0.6134(7) 0.081(3) Uani 1 2 d S T P . .
C00H C 0.5553(13) 0.250000 0.2757(10) 0.139(6) Uani 1 2 d S T P . .
H00D H 0.495745 0.172163 0.288760 0.209 Uiso 0.5 1 calc GR . . B -1
H00E H 0.590025 0.195922 0.226757 0.209 Uiso 0.5 1 calc GR . . B -1
H00F H 0.534395 0.381915 0.263342 0.209 Uiso 0.5 1 calc GR . . B -1
C00I C 0.7693(10) 0.250000 0.4267(11) 0.098(3) Uani 1 2 d S TU P . .
H00I H 0.837882 0.250000 0.443967 0.118 Uiso 1 2 calc RS T P . .
C9 C 0.7309(11) 0.250000 0.3432(11) 0.107(3) Uani 1 2 d S TU P . .
H9 H 0.770086 0.250000 0.293214 0.128 Uiso 1 2 calc RS T P . .
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'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C00C Au01 C00D 179.3(4) . . ?
C00D N007 C00B 124.0(10) . . ?
C00D N007 C00I 111.9(11) . . ?
C00I N007 C00B 124.1(11) . . ?
F003 C008 C00A 114.1(10) . . ?
F003 C008 C00C 119.7(10) . . ?
C00A C008 C00C 126.2(10) . . ?
C00D N8 C00H 126.7(11) . . ?
C00D N8 C9 107.7(12) . . ?
C9 N8 C00H 125.5(13) . . ?
F004 C00A C00F 117.1(10) . . ?
C008 C00A F004 123.7(11) . . ?
C008 C00A C00F 119.1(11) . . ?
N007 C00B H00A 109.5 . . ?
N007 C00B H00B 109.5 . . ?
N007 C00B H00C 109.5 . . ?
H00A C00B H00B 109.5 . . ?
H00A C00B H00C 109.5 . . ?
H00B C00B H00C 109.5 . . ?
C008 C00C Au01 124.0(7) . . ?
C00G C00C Au01 123.2(8) . . ?
C00G C00C C008 112.8(10) . . ?
N007 C00D Au01 126.0(8) . . ?
N007 C00D N8 107.9(10) . . ?
N8 C00D Au01 126.1(9) . . ?
F5 C00E C00G 115.6(13) . . ?
C00F C00E F5 122.5(13) . . ?
C00F C00E C00G 121.8(11) . . ?
C00A C00F Br02 121.1(10) . . ?
C00E C00F Br02 121.3(10) . . ?
C00E C00F C00A 117.6(11) . . ?
F6 C00G C00C 119.5(11) . . ?
F6 C00G C00E 118.1(10) . . ?
C00C C00G C00E 122.4(11) . . ?
N8 C00H H00D 109.5 . . ?
N8 C00H H00E 109.5 . . ?
N8 C00H H00F 109.5 . . ?
H00D C00H H00E 109.5 . . ?
H00D C00H H00F 109.5 . . ?
H00E C00H H00F 109.5 . . ?
N007 C00I H00I 127.8 . . ?
N007 C00I C9 104.4(13) . . ?
C9 C00I H00I 127.8 . . ?
N8 C9 H9 125.9 . . ?
C00I C9 N8 108.1(13) . . ?
C00I C9 H9 125.9 . . ?
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
Au01 C00C 2.020(10) . ?
Au01 C00D 2.025(10) . ?
Br02 C00F 1.869(12) . ?
F003 C008 1.344(11) . ?
F004 C00A 1.347(14) . ?
F6 C00G 1.330(13) . ?
F5 C00E 1.351(14) . ?
N007 C00B 1.463(16) . ?
N007 C00D 1.333(15) . ?
N007 C00I 1.372(16) . ?
C008 C00A 1.344(16) . ?
C008 C00C 1.391(15) . ?
N8 C00D 1.351(14) . ?
N8 C00H 1.427(18) . ?
N8 C9 1.395(17) . ?
C00A C00F 1.424(17) . ?
C00B H00A 0.9600 . ?
C00B H00B 0.9600 . ?
C00B H00C 0.9600 . ?
C00C C00G 1.382(15) . ?
C00E C00F 1.315(18) . ?
C00E C00G 1.427(18) . ?
C00H H00D 0.9600 . ?
C00H H00E 0.9600 . ?
C00H H00F 0.9600 . ?
C00I H00I 0.9300 . ?
C00I C9 1.39(2) . ?
C9 H9 0.9300 . ?
