#------------------------------------------------------------------------------
#$Date: 2025-03-04 22:12:27 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298255 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/36/1573662.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_1573662
loop_
_publ_author_name
'Dziewiątkowska, Róża'
'Krzeszczakowska, Joanna'
'Głodek, Marta'
'Łomzik, Michał'
'Plażuk, Damian'
'Makal, Anna'
_publ_section_title
;
 Pressure-induced phase transitions in a new luminescent
 gold(I)-arylacetylide.
;
_journal_issue                   8
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3362
_journal_page_last               3374
_journal_paper_doi               10.1039/d4dt03036b
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C15 H22 Au O P'
_chemical_formula_sum            'C15 H22 Au O P'
_chemical_formula_weight         446.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-15
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-07-24 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.9137(6)
_cell_length_b                   9.8518(5)
_cell_length_c                   16.3267(11)
_cell_measurement_reflns_used    4031
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.1560
_cell_measurement_theta_min      1.8870
_cell_volume                     2720.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment
'Diamond Anvil Cell filled with n-pentane/i-pentane 1:1 mixture'
_diffrn_ambient_pressure         2310000
_diffrn_ambient_temperature      293(2)
_diffrn_crystal_treatment
'pressurized rapidly in n-pentane/i-pentane 1:1 mixture as a hydrostatic medium'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0128
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.700
_diffrn_measured_fraction_theta_max 0.572
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00 -18.00   1.00  150.00    --   22.11 135.00 -57.00   36
  2  ω    -75.00  -6.00   1.00  150.00    --  -22.19  97.00 143.00   69
  3  ω    -60.00   5.00   1.00  150.00    --  -22.19  67.00 -23.00   65
  4  ω    -16.00  33.00   1.00  150.00    --  -22.19 -38.00-180.00   49
  5  ω    -97.00 -26.00   1.00  150.00    --  -22.19 135.00 -57.00   71
  6  ω    -38.00  -9.00   1.00  150.00    --  -22.19  77.00 -30.00   29
  7  ω    -56.00 -25.00   1.00  150.00    --  -22.19  38.00-180.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support
'Diamond Anvil Cell, effective opening angle 38 deg.'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0031586141
_diffrn_orient_matrix_UB_12      -0.0326779714
_diffrn_orient_matrix_UB_13      -0.0278252837
_diffrn_orient_matrix_UB_21      -0.0329219837
_diffrn_orient_matrix_UB_22      0.0041574214
_diffrn_orient_matrix_UB_23      0.0022131378
_diffrn_orient_matrix_UB_31      0.0007334630
_diffrn_orient_matrix_UB_32      0.0462661401
_diffrn_orient_matrix_UB_33      -0.0198445437
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ag K\a'
_diffrn_radiation_wavelength     0.56087
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_Laue_measured_fraction_full 0.700
_diffrn_reflns_Laue_measured_fraction_max 0.572
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13822
_diffrn_reflns_point_group_measured_fraction_full 0.700
_diffrn_reflns_point_group_measured_fraction_max 0.572
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         25.622
_diffrn_reflns_theta_min         1.900
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Ag) X-ray Source'
_exptl_absorpt_coefficient_mu    5.902
_exptl_absorpt_correction_T_max  0.59658
_exptl_absorpt_correction_T_min  0.58798
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    2.179
_exptl_crystal_description       needle
_exptl_crystal_F_000             1712
_exptl_crystal_preparation
'Mounted in a Diamond-Anvil Cell using n-pentane/i-pentane 1:1 mixture as pressure medium.,Luminescent'
_exptl_crystal_pressure_history
'Pressurized to 2.31 GPa and left to stabilize over ? hours.'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-pentane/dichloromethane'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_size_rad          0.400
_refine_diff_density_max         3.094
_refine_diff_density_min         -2.572
_refine_diff_density_rms         0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0830
_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)+138.6905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1640
_refine_ls_wR_factor_ref         0.1808
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1903
_reflns_number_total             2984
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt03036b2.cif
_cod_data_source_block           appr6_2p31GPa
_cod_depositor_comments
'Adding full bibliography for 1573624--1573666.cif.'
_cod_database_code               1573662
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H22 O P Au'
_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.
;
_diffrn_orient_matrix_axis[1]    matrixX
_diffrn_orient_matrix_axis[2]    matrixY
_diffrn_orient_matrix_axis[3]    matrixZ
_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. Uiso/Uaniso restraints and constraints
Uanis(C11) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C14(H14A,H14B)
3.b Me refined with riding coordinates:
 C11(H11A,H11B,H11C)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C4(H4), C5(H5)
3.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C9(H9A,H9B,H9C)
;
_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 1.185
_oxdiff_exptl_absorpt_empirical_full_min 0.853
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
Au1 Au 0.38310(4) 0.87081(6) 0.34272(5) 0.0297(2) Uani 1 1 d . . . . .
P1 P 0.3764(3) 1.0629(4) 0.2656(3) 0.0246(11) Uani 1 1 d . . . . .
O1 O 0.3356(7) 0.0592(14) 0.5539(11) 0.042(4) Uani 1 1 d . . . . .
C6 C 0.3558(11) 0.1812(19) 0.5175(15) 0.040(6) Uani 1 1 d . . . . .
C3 C 0.3743(9) 0.4349(18) 0.4505(13) 0.028(4) Uani 1 1 d . . . . .
C10 C 0.3927(9) 1.0238(18) 0.1584(15) 0.036(5) Uani 1 1 d . . . . .
H10A H 0.360066 1.083870 0.125627 0.043 Uiso 1 1 calc R U . . .
H10B H 0.447439 1.043053 0.145223 0.043 Uiso 1 1 calc R U . . .
C8 C 0.4402(10) 0.3605(18) 0.4738(14) 0.032(5) Uani 1 1 d . . . . .
H8 H 0.490795 0.395317 0.466193 0.038 Uiso 1 1 calc R U . . .
C2 C 0.3853(11) 0.5722(18) 0.4173(14) 0.035(5) Uani 1 1 d . . . . .
C12 C 0.2817(10) 1.149(2) 0.2718(17) 0.042(6) Uani 1 1 d . . . . .
H12A H 0.271127 1.174036 0.328224 0.050 Uiso 1 1 calc R U . . .
H12B H 0.283685 1.231944 0.239587 0.050 Uiso 1 1 calc R U . . .
C7 C 0.4297(9) 0.2341(18) 0.5083(13) 0.028(4) Uani 1 1 d . . . . .
H7 H 0.473398 0.184494 0.525465 0.033 Uiso 1 1 calc R U . . .
C15 C 0.4393(11) 1.324(2) 0.2472(17) 0.046(6) Uani 1 1 d . . . . .
H15A H 0.432066 1.310838 0.189413 0.068 Uiso 1 1 calc R U . . .
H15B H 0.484592 1.380579 0.256404 0.068 Uiso 1 1 calc R U . . .
H15C H 0.393172 1.366638 0.269803 0.068 Uiso 1 1 calc R U . . .
C14 C 0.4516(11) 1.191(2) 0.2873(15) 0.040(5) Uani 1 1 d . . . . .
H14A H 0.453838 1.204696 0.346053 0.048 Uiso 1 1 calc R U . . .
H14B H 0.502603 1.155402 0.270267 0.048 Uiso 1 1 calc R U . . .
C4 C 0.3013(10) 0.386(2) 0.4589(15) 0.037(5) Uani 1 1 d . . . . .
H4 H 0.258099 0.436783 0.441120 0.044 Uiso 1 1 calc R U . . .
C1 C 0.3890(10) 0.6866(19) 0.3948(14) 0.032(5) Uani 1 1 d . . . . .
C13 C 0.2157(11) 1.059(3) 0.2403(19) 0.053(7) Uani 1 1 d . . . . .
H13A H 0.229704 1.024386 0.187382 0.079 Uiso 1 1 calc R U . . .
H13B H 0.167893 1.111240 0.236091 0.079 Uiso 1 1 calc R U . . .
H13C H 0.207783 0.985173 0.277626 0.079 Uiso 1 1 calc R U . . .
C5 C 0.2897(9) 0.2554(19) 0.4954(14) 0.031(5) Uani 1 1 d . . . . .
H5 H 0.239163 0.221249 0.504073 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3968(13) -0.036(2) 0.5623(18) 0.050(7) Uani 1 1 d . . . . .
H9A H 0.429562 -0.034089 0.514375 0.075 Uiso 1 1 calc R U . . .
H9B H 0.374569 -0.124961 0.568848 0.075 Uiso 1 1 calc R U . . .
H9C H 0.428000 -0.013851 0.609601 0.075 Uiso 1 1 calc R U . . .
C11 C 0.3755(16) 0.885(3) 0.1350(19) 0.073(8) Uani 1 1 d . U . . .
H11A H 0.385672 0.873154 0.077608 0.110 Uiso 1 1 calc R U . . .
H11B H 0.408525 0.824100 0.165829 0.110 Uiso 1 1 calc R U . . .
H11C H 0.320981 0.864997 0.146194 0.110 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 0.0013 0.0009 '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 0.0058 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.0671 0.0586 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -0.6570 6.0260 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_axis.id
_axis.type
_axis.equipment
_axis.parity
_axis.depends_on
_axis.zero
_axis.vector[1]
_axis.vector[2]
_axis.vector[3]
source . source . . . 0.99999995 0.00000000 0.00030037
omega rotation goniometer -1 . 0.33691000 0.00000000 0.00000000 1.00000000
kappa rotation goniometer -1 omega 0.00043000 -0.76615415 0.00000000 0.64265684
phi rotation goniometer -1 kappa . 0.00004800 0.00000000 1.00000000
theta rotation goniometer -1 . 0.40100000 0.00000000 0.00000000 1.00000000
matrixX general general . phi . 1.00000000 0.00000000 0.00000000
matrixY general general . phi . 0.00000000 1.00000000 0.00000000
matrixZ general general . phi . 0.00000000 0.00000000 1.00000000
dacX translation general . phi . 0.00000000 1.00000000 0.00000000
dacY translation general . phi . -1.00000000 0.00000000 0.00000000
dacZ translation general . phi . 0.00000000 0.00000000 1.00000000
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
C1 Au1 P1 171.5(7) . . ?
C10 P1 Au1 110.5(6) . . ?
C10 P1 C12 106.6(10) . . ?
C10 P1 C14 103.2(10) . . ?
C12 P1 Au1 113.7(8) . . ?
C12 P1 C14 106.3(9) . . ?
C14 P1 Au1 115.6(8) . . ?
C6 O1 C9 116.1(15) . . ?
C7 C6 O1 127.3(17) . . ?
C7 C6 C5 120.7(17) . . ?
C5 C6 O1 111.8(16) . . ?
C8 C3 C2 119.1(15) . . ?
C4 C3 C8 121.8(17) . . ?
C4 C3 C2 119.1(16) . . ?
P1 C10 H10A 108.5 . . ?
P1 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 P1 115.1(16) . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C3 C8 H8 120.5 . . ?
C7 C8 C3 119.0(15) . . ?
C7 C8 H8 120.5 . . ?
C1 C2 C3 174(2) . . ?
P1 C12 H12A 109.5 . . ?
P1 C12 H12B 109.5 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 P1 110.9(15) . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C6 C7 C8 120.7(16) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
P1 C14 H14A 108.4 . . ?
P1 C14 H14B 108.4 . . ?
C15 C14 P1 115.3(15) . . ?
C15 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
H14A C14 H14B 107.5 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.5(16) . . ?
C5 C4 H4 120.3 . . ?
C2 C1 Au1 171(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C5 C4 118.3(15) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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 P1 2.275(4) . ?
Au1 C1 2.007(18) . ?
P1 C10 1.81(3) . ?
P1 C12 1.817(18) . ?
P1 C14 1.825(19) . ?
O1 C6 1.38(2) . ?
O1 C9 1.40(2) . ?
C6 C7 1.36(2) . ?
C6 C5 1.38(2) . ?
C3 C8 1.39(2) . ?
C3 C2 1.47(3) . ?
C3 C4 1.33(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.45(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.38(3) . ?
C2 C1 1.19(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.51(3) . ?
C7 H7 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 C14 1.48(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.43(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C5 H5 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
Au1 P1 C10 C11 23.5(18) . . . . ?
Au1 P1 C12 C13 -62(2) . . . . ?
Au1 P1 C14 C15 -170.2(15) . . . . ?
O1 C6 C7 C8 -177(2) . . . . ?
O1 C6 C5 C4 178(2) . . . . ?
C3 C8 C7 C6 2(3) . . . . ?
C3 C4 C5 C6 -3(4) . . . . ?
C10 P1 C12 C13 60(2) . . . . ?
C10 P1 C14 C15 69.1(19) . . . . ?
C8 C3 C4 C5 2(4) . . . . ?
C2 C3 C8 C7 177(2) . . . . ?
C2 C3 C4 C5 -177(2) . . . . ?
C12 P1 C10 C11 -100.6(18) . . . . ?
C12 P1 C14 C15 -43(2) . . . . ?
C7 C6 C5 C4 3(4) . . . . ?
C14 P1 C10 C11 147.7(18) . . . . ?
C14 P1 C12 C13 170.0(19) . . . . ?
C4 C3 C8 C7 -2(3) . . . . ?
C5 C6 C7 C8 -3(4) . . . . ?
C9 O1 C6 C7 -19(4) . . . . ?
C9 O1 C6 C5 167(2) . . . . ?
