#------------------------------------------------------------------------------
#$Date: 2023-09-05 21:58:48 +0200 (Tue 05 de Sep de 2023) $
#$Revision: 286150 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/68/7246812.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_7246812
loop_
_publ_author_name
'Do, Jean-Louis'
'Auvray, Thomas'
'Lennox, Cameron B.'
'Titi, Hatem M.'
'Cuccia, Louis A.'
'Friščić, Tomislav'
_publ_section_title
;
 Rapid, room-temperature, solvent-free mechanochemical oxidation of
 elemental gold into organosoluble gold salts
;
_journal_issue                   15
_journal_name_full               'Green Chemistry'
_journal_page_first              5899
_journal_page_last               5906
_journal_paper_doi               10.1039/D3GC01150J
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'Au Br4, C8 H20 N'
_chemical_formula_sum            'C8 H20 Au Br4 N'
_chemical_formula_weight         646.86
_chemical_properties_physical    Light-sensitive,Photo-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-23
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-12-06 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.562(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3812(3)
_cell_length_b                   8.2418(3)
_cell_length_c                   10.5053(4)
_cell_measurement_reflns_used    6832
_cell_measurement_temperature    298
_cell_measurement_theta_max      72.404
_cell_measurement_theta_min      8.287
_cell_volume                     812.21(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9295
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.469
_diffrn_reflns_theta_min         8.286
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    28.319
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1575 before and 0.0626 after correction.
The Ratio of minimum to maximum transmission is 0.6391.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.645
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.995
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     68
_refine_ls_number_reflns         1592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0280
_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)+(0.0373P)²+1.9087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0720
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1484
_reflns_number_total             1592
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc01150j2.cif
_cod_data_source_block           teaaubr4
_cod_depositor_comments
'Adding full bibliography for 7246811--7246815.cif.'
_cod_database_code               7246812
_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   0.281
_shelx_estimated_absorpt_t_min   0.164
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
;
_shelx_res_file
;
TITL teaaubr4_a.res in P2/n
    teaaubr4.res
    created by SHELXL-2018/3 at 09:33:53 on 23-Feb-2022
REM Old TITL TEAAuBr4 in P2/n
REM SHELXT solution in P2/n: R1 0.182, Rweak 0.003, Alpha 0.031
REM <I/s> 1.192 for 118 systematic absences, Orientation as input
REM Formula found by SHELXT: C6 N Br4 Au
CELL 1.54178 9.3812 8.2418 10.5053 90 90.562 90
ZERR 2 0.0003 0.0003 0.0004 0 0.002 0
LATT 1
SYMM 0.5-X,+Y,0.5-Z
SFAC C H Au Br N
UNIT 16 40 2 8 2

L.S. 10
PLAN  6
SIZE 0.1 0.07 0.06
TEMP 24.85
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\TEAAuBr4.hkl">
REM </olex2.extras>

WGHT    0.037300    1.908700
FVAR       0.37630
AU1   3    0.750000    0.651704    0.750000    10.50000    0.04329    0.02523 =
         0.05112    0.00000   -0.01232    0.00000
BR1   4    0.967753    0.650593    0.628198    11.00000    0.05722    0.06090 =
         0.07979   -0.01017    0.00763    0.00449
BR2   4    0.750000    0.359394    0.750000    10.50000    0.05274    0.02532 =
         0.19286    0.00000   -0.02148    0.00000
BR3   4    0.750000    0.944863    0.750000    10.50000    0.08148    0.02502 =
         0.08009    0.00000    0.00536    0.00000
N1    5    0.750000    0.870445    0.250000    10.50000    0.03347    0.05115 =
         0.04838    0.00000   -0.00714    0.00000
C1    1    0.620453    0.768336    0.276814    11.00000    0.04218    0.06152 =
         0.07407    0.00426   -0.01486   -0.00872
AFIX  23
H1A   2    0.597259    0.706046    0.201056    11.00000   -1.20000
H1B   2    0.540747    0.840100    0.293145    11.00000   -1.20000
AFIX   0
C2    1    0.635923    0.652409    0.387793    11.00000    0.08038    0.08909 =
         0.09560    0.03339   -0.02394   -0.03643
AFIX 137
H2A   2    0.712136    0.577741    0.371498    11.00000   -1.50000
H2B   2    0.548618    0.593366    0.398321    11.00000   -1.50000
H2C   2    0.656828    0.712574    0.463965    11.00000   -1.50000
AFIX   0
C3    1    0.789484    0.975068    0.363491    11.00000    0.05391    0.05749 =
         0.04933   -0.00046   -0.00617   -0.00779
AFIX  23
H3A   2    0.876558    1.033112    0.344095    11.00000   -1.20000
H3B   2    0.809779    0.904485    0.435298    11.00000   -1.20000
AFIX   0
C4    1    0.677776    1.097504    0.403313    11.00000    0.08368    0.07433 =
         0.06259   -0.01115    0.00692    0.00896
AFIX 137
H4A   2    0.662132    1.173930    0.335644    11.00000   -1.50000
H4B   2    0.710255    1.153907    0.478106    11.00000   -1.50000
H4C   2    0.590230    1.042175    0.421395    11.00000   -1.50000
AFIX   0
HKLF 4




REM  teaaubr4_a.res in P2/n
REM wR2 = 0.071970, GooF = S = 1.04274, Restrained GooF = 1.04274 for all data
REM R1 = 0.028020 for 1484 Fo > 4sig(Fo) and 0.030067 for all 1592 data
REM 68 parameters refined using 0 restraints

END

WGHT      0.0373      1.9088

REM Highest difference peak  0.874,  deepest hole -0.995,  1-sigma level  0.132
Q1    1   1.0077  0.6375  0.7004  11.00000  0.05    0.87
Q2    1   0.9188  0.5751  0.6167  11.00000  0.05    0.87
Q3    1   0.7570  0.4083  0.8226  11.00000  0.05    0.70
Q4    1   0.7813  0.4955  0.7172  11.00000  0.05    0.67
Q5    1   0.7920  0.8015  0.7196  11.00000  0.05    0.59
Q6    1   0.8041  0.9074  0.8089  11.00000  0.05    0.48
;
_shelx_res_checksum              98334
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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
Au1 Au 0.750000 0.65170(3) 0.750000 0.03997(13) Uani 1 2 d S T P . .
Br1 Br 0.96775(7) 0.65059(8) 0.62820(7) 0.0659(2) Uani 1 1 d . . . . .
Br2 Br 0.750000 0.35939(9) 0.750000 0.0905(5) Uani 1 2 d S T P . .
Br3 Br 0.750000 0.94486(9) 0.750000 0.0622(2) Uani 1 2 d S T P . .
N1 N 0.750000 0.8704(7) 0.250000 0.0444(13) Uani 1 2 d S T P . .
C1 C 0.6205(6) 0.7683(8) 0.2768(6) 0.0594(14) Uani 1 1 d . . . . .
H1A H 0.597259 0.706046 0.201056 0.071 Uiso 1 1 calc R U . . .
H1B H 0.540747 0.840100 0.293145 0.071 Uiso 1 1 calc R U . . .
C2 C 0.6359(9) 0.6524(10) 0.3878(9) 0.089(3) Uani 1 1 d . . . . .
H2A H 0.712136 0.577741 0.371498 0.133 Uiso 1 1 calc R U . . .
H2B H 0.548618 0.593366 0.398321 0.133 Uiso 1 1 calc R U . . .
H2C H 0.656828 0.712574 0.463965 0.133 Uiso 1 1 calc R U . . .
C3 C 0.7895(6) 0.9751(7) 0.3635(5) 0.0536(12) Uani 1 1 d . . . . .
H3A H 0.876558 1.033112 0.344095 0.064 Uiso 1 1 calc R U . . .
H3B H 0.809779 0.904485 0.435298 0.064 Uiso 1 1 calc R U . . .
C4 C 0.6778(8) 1.0975(9) 0.4033(7) 0.0735(18) Uani 1 1 d . . . . .
H4A H 0.662132 1.173930 0.335644 0.110 Uiso 1 1 calc R U . . .
H4B H 0.710255 1.153907 0.478106 0.110 Uiso 1 1 calc R U . . .
H4C H 0.590230 1.042175 0.421395 0.110 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Au1 0.04329(18) 0.02523(17) 0.05112(19) 0.000 -0.01232(12) 0.000
Br1 0.0572(4) 0.0609(4) 0.0798(5) -0.0102(3) 0.0076(3) 0.0045(3)
Br2 0.0527(5) 0.0253(4) 0.1929(14) 0.000 -0.0215(7) 0.000
Br3 0.0815(6) 0.0250(4) 0.0801(6) 0.000 0.0054(4) 0.000
N1 0.033(3) 0.051(3) 0.048(3) 0.000 -0.007(2) 0.000
C1 0.042(3) 0.062(3) 0.074(4) 0.004(3) -0.015(3) -0.009(3)
C2 0.080(5) 0.089(6) 0.096(6) 0.033(4) -0.024(4) -0.036(4)
C3 0.054(3) 0.057(3) 0.049(3) 0.000(2) -0.006(2) -0.008(2)
C4 0.084(5) 0.074(4) 0.063(4) -0.011(3) 0.007(3) 0.009(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -4.4197 7.2980 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
Br1 Au1 Br1 179.57(3) . 2_656 ?
Br2 Au1 Br1 89.783(16) . 2_656 ?
Br2 Au1 Br1 89.783(16) . . ?
Br2 Au1 Br3 180.0 . . ?
Br3 Au1 Br1 90.217(16) . . ?
Br3 Au1 Br1 90.217(16) . 2_656 ?
C1 N1 C1 112.1(7) 2_655 . ?
C1 N1 C3 105.9(3) 2_655 . ?
C1 N1 C3 111.2(3) . . ?
C1 N1 C3 105.9(3) . 2_655 ?
C1 N1 C3 111.2(3) 2_655 2_655 ?
C3 N1 C3 110.6(6) 2_655 . ?
N1 C1 H1A 108.5 . . ?
N1 C1 H1B 108.5 . . ?
N1 C1 C2 115.2(5) . . ?
H1A C1 H1B 107.5 . . ?
C2 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 108.4 . . ?
N1 C3 H3B 108.4 . . ?
N1 C3 C4 115.6(5) . . ?
H3A C3 H3B 107.4 . . ?
C4 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 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
Au1 Br1 2.4211(7) . ?
Au1 Br1 2.4211(7) 2_656 ?
Au1 Br2 2.4092(8) . ?
Au1 Br3 2.4162(7) . ?
N1 C1 1.507(6) . ?
N1 C1 1.507(6) 2_655 ?
N1 C3 1.514(6) 2_655 ?
N1 C3 1.514(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.513(10) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.517(9) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 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
C1 N1 C1 C2 58.4(6) 2_655 . . . ?
C1 N1 C3 C4 176.1(6) 2_655 . . . ?
C1 N1 C3 C4 -61.8(7) . . . . ?
C3 N1 C1 C2 179.8(6) 2_655 . . . ?
C3 N1 C1 C2 -60.0(8) . . . . ?
C3 N1 C3 C4 55.5(5) 2_655 . . . ?
