#------------------------------------------------------------------------------
#$Date: 2023-04-20 13:53:48 +0200 (Thu 20 de Apr de 2023) $
#$Revision: 282777 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/96/1519680.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_1519680
loop_
_publ_author_name
'Vidal, C.'
'Merz, L.'
'García-Álvarez, J.'
_publ_section_title
;
 Deep eutectic solvents: biorenewable reaction media for Au( <scp>i</scp>
 )-catalysed cycloisomerisations and one-pot tandem
 cycloisomerisation/Diels--Alder reactions
;
_journal_issue                   7
_journal_name_full               'Green Chemistry'
_journal_page_first              3870
_journal_page_last               3878
_journal_paper_doi               10.1039/C5GC00656B
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C49 H42 Au2 Cl2 N2 O4 P4 S2'
_chemical_formula_sum            'C49 H42 Au2 Cl2 N2 O4 P4 S2'
_chemical_formula_weight         1375.37
_chemical_name_systematic        3
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-01-23 deposited with the CCDC.
2015-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 122.413(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.848(2)
_cell_length_b                   11.2564(5)
_cell_length_c                   20.6909(16)
_cell_measurement_reflns_used    6519
_cell_measurement_temperature    297(14)
_cell_measurement_theta_max      68.8700
_cell_measurement_theta_min      4.4640
_cell_volume                     5082.2(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      297(14)
_diffrn_detector_area_resol_mean 8.2640
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12034
_diffrn_reflns_theta_full        69.56
_diffrn_reflns_theta_max         69.56
_diffrn_reflns_theta_min         4.48
_diffrn_standards_number         6313
_exptl_absorpt_coefficient_mu    13.989
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2280
_exptl_crystal_recrystallization_method 'Bi-phasic media '
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.0400
_exptl_crystal_size_min          0.0200
_refine_diff_density_max         0.970
_refine_diff_density_min         -1.960
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0536P)²+23.0145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1241
_reflns_number_gt                4020
_reflns_number_total             4673
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5gc00656b2.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_cell_volume        5082.2(6)
_cod_database_code               1519680
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.5000 0.6647(7) 0.7500 0.0437(17) Uani 1 2 d S
C2 C 0.3695(3) 0.6448(6) 0.6811(3) 0.0469(13) Uani 1 1 d .
C3 C 0.3114(3) 0.6921(8) 0.6383(5) 0.073(2) Uani 1 1 d .
H3 H 0.3059 0.7741 0.6351 0.088 Uiso 1 1 calc R
C4 C 0.2617(4) 0.6176(10) 0.6004(7) 0.100(3) Uani 1 1 d .
H4 H 0.2225 0.6498 0.5712 0.120 Uiso 1 1 calc R
C5 C 0.2688(4) 0.4974(9) 0.6051(7) 0.090(3) Uani 1 1 d .
H5 H 0.2347 0.4481 0.5790 0.107 Uiso 1 1 calc R
C6 C 0.3265(4) 0.4490(7) 0.6483(5) 0.073(2) Uani 1 1 d .
H6 H 0.3314 0.3670 0.6522 0.088 Uiso 1 1 calc R
C7 C 0.3776(4) 0.5230(6) 0.6861(4) 0.0577(16) Uani 1 1 d .
H7 H 0.4168 0.4906 0.7145 0.069 Uiso 1 1 calc R
C8 C 0.4202(3) 0.8682(5) 0.6712(3) 0.0449(13) Uani 1 1 d .
C9 C 0.4221(4) 0.9829(6) 0.6962(5) 0.070(2) Uani 1 1 d .
H9 H 0.4278 0.9960 0.7440 0.084 Uiso 1 1 calc R
C10 C 0.4154(5) 1.0780(7) 0.6501(6) 0.090(3) Uani 1 1 d .
H10 H 0.4167 1.1552 0.6669 0.108 Uiso 1 1 calc R
C11 C 0.4069(5) 1.0588(9) 0.5800(6) 0.088(3) Uani 1 1 d .
H11 H 0.4028 1.1233 0.5495 0.106 Uiso 1 1 calc R
C12 C 0.4045(4) 0.9466(9) 0.5541(5) 0.076(2) Uani 1 1 d .
H12 H 0.3982 0.9350 0.5059 0.092 Uiso 1 1 calc R
C13 C 0.4113(3) 0.8485(7) 0.5998(4) 0.0589(17) Uani 1 1 d .
H13 H 0.4098 0.7715 0.5824 0.071 Uiso 1 1 calc R
C14 C 0.3569(3) 0.6083(7) 0.8811(4) 0.0562(16) Uani 1 1 d .
C15 C 0.3565(4) 0.4877(7) 0.8741(6) 0.077(2) Uani 1 1 d .
H15 H 0.3707 0.4528 0.8456 0.092 Uiso 1 1 calc R
C16 C 0.3351(4) 0.4184(9) 0.9096(6) 0.091(3) Uani 1 1 d .
H16 H 0.3340 0.3363 0.9039 0.109 Uiso 1 1 calc R
C17 C 0.3158(6) 0.4664(12) 0.9522(7) 0.104(4) Uani 1 1 d .
H17 H 0.3016 0.4184 0.9761 0.125 Uiso 1 1 calc R
C18 C 0.3172(6) 0.5877(12) 0.9602(7) 0.111(4) Uani 1 1 d .
H18 H 0.3047 0.6215 0.9907 0.133 Uiso 1 1 calc R
C19 C 0.3370(5) 0.6609(9) 0.9234(5) 0.088(3) Uani 1 1 d .
H19 H 0.3368 0.7431 0.9276 0.106 Uiso 1 1 calc R
C20 C 0.3921(3) 0.9703(6) 0.8647(4) 0.0537(15) Uani 1 1 d .
C21 C 0.3318(4) 0.9663(9) 0.8100(6) 0.090(3) Uani 1 1 d .
H21 H 0.3095 0.8969 0.8012 0.108 Uiso 1 1 calc R
C22 C 0.3041(5) 1.0667(11) 0.7677(8) 0.119(4) Uani 1 1 d .
H22 H 0.2628 1.0647 0.7292 0.142 Uiso 1 1 calc R
C23 C 0.3365(6) 1.1694(9) 0.7813(7) 0.104(3) Uani 1 1 d .
H23 H 0.3171 1.2371 0.7527 0.125 Uiso 1 1 calc R
C24 C 0.3973(5) 1.1724(8) 0.8369(6) 0.085(3) Uani 1 1 d .
H24 H 0.4195 1.2421 0.8461 0.101 Uiso 1 1 calc R
C25 C 0.4259(4) 1.0718(7) 0.8796(5) 0.070(2) Uani 1 1 d .
H25 H 0.4673 1.0730 0.9177 0.084 Uiso 1 1 calc R
Au1 Au 0.513027(15) 0.51581(3) 0.913782(18) 0.06322(14) Uani 1 1 d .
Cl1 Cl 0.52206(13) 0.3566(2) 0.85423(15) 0.0910(7) Uani 1 1 d .
N1 N 0.4411(2) 0.7950(4) 0.8093(3) 0.0459(11) Uani 1 1 d .
O1 O 0.3745(2) 0.6762(4) 0.8393(2) 0.0535(10) Uani 1 1 d .
O2 O 0.4228(2) 0.8704(4) 0.9107(3) 0.0602(12) Uani 1 1 d .
P1 P 0.43301(7) 0.74556(12) 0.73267(8) 0.0395(3) Uani 1 1 d .
P2 P 0.43488(7) 0.75519(13) 0.87614(9) 0.0454(3) Uani 1 1 d .
S1 S 0.50423(9) 0.68076(17) 0.97012(10) 0.0648(4) Uani 1 1 d .
H1 H 0.490(3) 0.617(6) 0.710(4) 0.056(19) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 -4.4200 7.2980 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3640 0.7020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2960 0.4330 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3330 0.5570 '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
P1 C1 P1 119.7(5) . 2_656
P1 C1 H1 111(4) . .
P1 C1 H1 105(4) 2_656 .
C3 C2 C7 120.0(7) . .
C3 C2 P1 118.1(5) . .
C7 C2 P1 121.9(5) . .
C4 C3 C2 119.7(8) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C5 C4 C3 121.0(9) . .
C5 C4 H4 119.5 . .
C3 C4 H4 119.5 . .
C4 C5 C6 119.9(8) . .
C4 C5 H5 120.1 . .
C6 C5 H5 120.1 . .
C5 C6 C7 120.0(8) . .
C5 C6 H6 120.0 . .
C7 C6 H6 120.0 . .
C2 C7 C6 119.4(8) . .
C2 C7 H7 120.3 . .
C6 C7 H7 120.3 . .
C9 C8 C13 120.1(6) . .
C9 C8 P1 120.0(5) . .
C13 C8 P1 119.8(5) . .
C8 C9 C10 119.8(8) . .
C8 C9 H9 120.1 . .
C10 C9 H9 120.1 . .
C11 C10 C9 120.1(9) . .
C11 C10 H10 119.9 . .
C9 C10 H10 119.9 . .
C12 C11 C10 120.9(7) . .
C12 C11 H11 119.5 . .
C10 C11 H11 119.5 . .
C11 C12 C13 120.2(8) . .
C11 C12 H12 119.9 . .
C13 C12 H12 119.9 . .
C8 C13 C12 118.8(7) . .
C8 C13 H13 120.6 . .
C12 C13 H13 120.6 . .
C19 C14 C15 121.1(7) . .
C19 C14 O1 121.2(7) . .
C15 C14 O1 117.5(7) . .
C14 C15 C16 119.2(9) . .
C14 C15 H15 120.4 . .
C16 C15 H15 120.4 . .
C17 C16 C15 121.5(10) . .
C17 C16 H16 119.3 . .
C15 C16 H16 119.3 . .
C16 C17 C18 119.1(9) . .
C16 C17 H17 120.5 . .
C18 C17 H17 120.5 . .
C17 C18 C19 121.1(10) . .
C17 C18 H18 119.5 . .
C19 C18 H18 119.5 . .
C14 C19 C18 118.0(10) . .
C14 C19 H19 121.0 . .
C18 C19 H19 121.0 . .
C21 C20 C25 121.8(8) . .
C21 C20 O2 121.2(7) . .
C25 C20 O2 116.9(7) . .
C20 C21 C22 118.7(9) . .
C20 C21 H21 120.6 . .
C22 C21 H21 120.6 . .
C23 C22 C21 120.9(10) . .
C23 C22 H22 119.5 . .
C21 C22 H22 119.5 . .
C22 C23 C24 119.8(9) . .
C22 C23 H23 120.1 . .
C24 C23 H23 120.1 . .
C23 C24 C25 120.0(9) . .
C23 C24 H24 120.0 . .
C25 C24 H24 120.0 . .
C20 C25 C24 118.8(8) . .
C20 C25 H25 120.6 . .
C24 C25 H25 120.6 . .
Cl1 Au1 S1 177.60(7) . .
P2 N1 P1 140.7(3) . .
C14 O1 P2 124.7(4) . .
C20 O2 P2 121.4(4) . .
N1 P1 C8 108.4(3) . .
N1 P1 C2 113.8(3) . .
C8 P1 C2 107.7(3) . .
N1 P1 C1 112.2(2) . .
C8 P1 C1 108.8(3) . .
C2 P1 C1 105.7(3) . .
N1 P2 O1 106.2(3) . .
N1 P2 O2 107.9(3) . .
O1 P2 O2 107.1(3) . .
N1 P2 S1 121.8(2) . .
O1 P2 S1 111.78(19) . .
O2 P2 S1 101.2(2) . .
P2 S1 Au1 97.38(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 P1 1.814(4) .
C1 P1 1.814(4) 2_656
C1 H1 0.90(7) .
C2 C3 1.378(10) .
C2 C7 1.383(9) .
C2 P1 1.800(6) .
C3 C4 1.376(12) .
C3 H3 0.9300 .
C4 C5 1.363(14) .
C4 H4 0.9300 .
C5 C6 1.374(14) .
C5 H5 0.9300 .
C6 C7 1.393(11) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C9 1.382(10) .
C8 C13 1.386(9) .
C8 P1 1.784(6) .
C9 C10 1.383(11) .
C9 H9 0.9300 .
C10 C11 1.362(14) .
C10 H10 0.9300 .
C11 C12 1.360(15) .
C11 H11 0.9300 .
C12 C13 1.402(11) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 C19 1.365(11) .
C14 C15 1.364(11) .
C14 O1 1.401(7) .
C15 C16 1.377(12) .
C15 H15 0.9300 .
C16 C17 1.339(16) .
C16 H16 0.9300 .
C17 C18 1.373(18) .
C17 H17 0.9300 .
C18 C19 1.393(13) .
C18 H18 0.9300 .
C19 H19 0.9300 .
C20 C21 1.349(12) .
C20 C25 1.369(11) .
C20 O2 1.411(9) .
C21 C22 1.372(15) .
C21 H21 0.9300 .
C22 C23 1.364(17) .
C22 H22 0.9300 .
C23 C24 1.362(15) .
C23 H23 0.9300 .
C24 C25 1.381(13) .
C24 H24 0.9300 .
C25 H25 0.9300 .
Au1 Cl1 2.257(2) .
Au1 S1 2.268(2) .
N1 P2 1.543(5) .
N1 P1 1.584(5) .
O1 P2 1.591(5) .
O2 P2 1.591(5) .
P2 S1 1.990(2) .
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
C7 C2 C3 C4 -0.3(12) .
P1 C2 C3 C4 -177.6(8) .
C2 C3 C4 C5 0.6(17) .
C3 C4 C5 C6 0.1(18) .
C4 C5 C6 C7 -1.1(16) .
C3 C2 C7 C6 -0.7(11) .
P1 C2 C7 C6 176.5(6) .
C5 C6 C7 C2 1.4(12) .
C13 C8 C9 C10 -0.5(13) .
P1 C8 C9 C10 176.6(7) .
C8 C9 C10 C11 0.1(15) .
C9 C10 C11 C12 0.5(16) .
C10 C11 C12 C13 -0.7(14) .
C9 C8 C13 C12 0.3(11) .
P1 C8 C13 C12 -176.8(5) .
C11 C12 C13 C8 0.3(12) .
C19 C14 C15 C16 0.8(14) .
O1 C14 C15 C16 -175.1(8) .
C14 C15 C16 C17 -1.5(16) .
C15 C16 C17 C18 0.3(18) .
C16 C17 C18 C19 1.4(19) .
C15 C14 C19 C18 0.9(15) .
O1 C14 C19 C18 176.7(9) .
C17 C18 C19 C14 -2.0(18) .
C25 C20 C21 C22 0.9(15) .
O2 C20 C21 C22 179.0(10) .
C20 C21 C22 C23 -1(2) .
C21 C22 C23 C24 1(2) .
C22 C23 C24 C25 -0.4(17) .
C21 C20 C25 C24 -0.5(12) .
O2 C20 C25 C24 -178.6(7) .
C23 C24 C25 C20 0.2(13) .
C19 C14 O1 P2 70.4(9) .
C15 C14 O1 P2 -113.7(7) .
C21 C20 O2 P2 69.3(9) .
C25 C20 O2 P2 -112.5(6) .
P2 N1 P1 C8 156.5(5) .
P2 N1 P1 C2 36.7(7) .
P2 N1 P1 C1 -83.3(6) .
C9 C8 P1 N1 3.4(7) .
C13 C8 P1 N1 -179.5(5) .
C9 C8 P1 C2 126.9(6) .
C13 C8 P1 C2 -56.0(6) .
C9 C8 P1 C1 -118.9(6) .
C13 C8 P1 C1 58.2(6) .
C3 C2 P1 N1 77.9(6) .
C7 C2 P1 N1 -99.3(6) .
C3 C2 P1 C8 -42.3(6) .
C7 C2 P1 C8 140.4(5) .
C3 C2 P1 C1 -158.4(5) .
C7 C2 P1 C1 24.3(6) .
P1 C1 P1 N1 -78.4(2) 2_656
P1 C1 P1 C8 41.6(2) 2_656
P1 C1 P1 C2 157.0(2) 2_656
P1 N1 P2 O1 -40.5(6) .
P1 N1 P2 O2 -155.1(5) .
P1 N1 P2 S1 88.9(6) .
C14 O1 P2 N1 170.2(5) .
C14 O1 P2 O2 -74.7(6) .
C14 O1 P2 S1 35.3(6) .
C20 O2 P2 N1 29.8(6) .
C20 O2 P2 O1 -84.1(5) .
C20 O2 P2 S1 158.7(5) .
N1 P2 S1 Au1 -63.3(2) .
O1 P2 S1 Au1 63.62(19) .
O2 P2 S1 Au1 177.30(19) .
Cl1 Au1 S1 P2 53(2) .
